Researcher Profile and Settings

Master

Affiliation (Master)

• Institute for Catalysis　Molecular Catalyst Research Division

Affiliation (Master)

• Institute for Catalysis　Molecular Catalyst Research Division

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Profile and Settings

Affiliation

• Hokkaido University, Graduate School of Engineering Molecular and Macromolecular Chemistry 1

Degree

• Ph. D（2002/03 Hokkaido University）

Profile and Settings

• Name (Japanese)

  Uraguchi

• Name (Kana)

  Daisuke

• Name

  I-6592-2014, 200901053718216715

Affiliation

• Hokkaido University, Graduate School of Engineering Molecular and Macromolecular Chemistry 1

Achievement

Research Interests

• organic chemistry   

Research Areas

• Nanotechnology/Materials / Synthetic organic chemistry

Research Experience

• 2020/11 Hokkaido University Institute for Catalysis Professor
• 2011/10 - 2020/10 Associate Professor
• 2008/01 - 2011/09 Associate Professor
• 2007/04 - 2007/12 Assistant Professor
• 2006/05 - 2007/03 Assistant Professor
• 2004/10 - 2006/04 Sagami Chemical Research Center (Researcher)
• 2002/04 - 2004/10 日本学術振興会特別研究員(PD)
• 2000/01 - 2002/03 日本学術振興会特別研究員(DC2)

Published Papers

• trans-Cyclooctenes as Scavengers of Bromine Involved in Catalytic Bromination

  Ryuichi Murata, Kenta Shitamichi, Masatsugu Hiramatsu, Seijiro Matsubara, Daisuke Uraguchi, Keisuke Asano

  Chemistry - A European Journal 30 (8) 0947-6539 2024/02/07 

  Scavengers that capture reactive chemical substances are used to prevent the decomposition of materials. However, in the field of catalysis, the development of scavengers that inhibit background pathways has attracted little attention, although the concept will open up an otherwise inaccessible reaction space. In catalytic bromination, fast non-catalyzed background reactions disturb the catalytic control of the selectivity, even when using N-bromoamide reagents, which have a milder reactivity than bromine (Br2). Here, we developed a trans-cyclooctene (TCO) bearing a 2-pyridylethyl group to efficiently retard background reactions by capturing Br2 in bromocyclization using N-bromosuccinimide. The use of less than a stoichiometric amount of the TCO was sufficient to inhibit non-catalyzed reactions, and mechanistic studies using the TCO revealed that in situ-generated Br2 provides non-catalyzed reaction pathways based on a chain mechanism. The TCO is useful as an additive for improving enantioselectivity and regioselectivity in catalytic reactions. Cooperative systems using the TCO with selective catalysts offer an alternative strategy for optimizing catalyst-controlled selectivity during bromination. Moreover, it also served as an indicator of Br2 involved in catalytic reaction pathways; thus, the TCO was useful as a probe for mechanistic investigations into the involvement of Br2 in bromination reactions of interest.
• o-Quinone methide with overcrowded olefinic core as a catalytically-active surrogate of triarylmethylium salt for dehydridative oxidation of benzylic alcohols under aerobic photoirradiation conditions

  Kohsuke Kato, Daisuke Uraguchi, Takashi Ooi

  Tetrahedron 132459 - 132459 0040-4020 2021/09
• o-Quinone methide with overcrowded olefin component as a dehydridation catalyst under aerobic photoirradiation conditions

  Daisuke Uraguchi, Kohsuke Kato, Takashi Ooi

  Chemical Science 12 (8) 2778 - 2783 2041-6520 2021 

  An o-quinone methide (o-QM) featuring an overcrowded olefinic framework is introduced, which exhibits dehydridation activity owing to its enhanced zwitterionic character, particularly through photoexcitation.

• Catalytic asymmetric synthesis of 5-membered alicyclic α-quaternary β-amino acids via [3 + 2]-photocycloaddition of α-substituted acrylates

  Yuto Kimura, Daisuke Uraguchi, Takashi Ooi

  Organic & Biomolecular Chemistry 2021
• Urea as a Redox-Active Directing Group under Asymmetric Photocatalysis of Iridium-Chiral Borate Ion Pairs

  Daisuke Uraguchi, Yuto Kimura, Fumito Ueoka, Takashi Ooi

  Journal of the American Chemical Society 2020/11/18
• A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis

  Daisuke Uraguchi, Fumito Ueoka, Naoya Tanaka, Tomohito Kizu, Wakana Takahashi, Takashi Ooi

  Angewandte Chemie International Edition 59 (28) 11456 - 11461 2020/07/06
• A Structurally Robust Chiral Borate Ion: Molecular Design, Synthesis, and Asymmetric Catalysis

  Daisuke Uraguchi, Fumito Ueoka, Naoya Tanaka, Tomohito Kizu, Wakana Takahashi, Takashi Ooi

  Angewandte Chemie 132 (28) 11553 - 11558 2020/07/06
• Unveiling Latent Photoreactivity of Imines

  Daisuke Uraguchi, Yuto Tsuchiya, Tsuyoshi Ohtani, Takafumi Enomoto, Shigeyuki Masaoka, Daisuke Yokogawa, Takashi Ooi

  Angewandte Chemie 132 (9) 3694 - 3699 2020/02/24
• Unveiling Latent Photoreactivity of Imines

  Daisuke Uraguchi, Yuto Tsuchiya, Tsuyoshi Ohtani, Takafumi Enomoto, Shigeyuki Masaoka, Daisuke Yokogawa, Takashi Ooi

  Angewandte Chemie International Edition 59 (9) 3665 - 3670 1433-7851 2020/02/24 [Refereed][Not invited]
   

  Unlike carbonyl compounds, it has long been common understanding that excited imines show virtually no photoreactivity, and hence their properties and potential utility in chemical science remain largely unexplored. Now, a strategy is presented for eliciting latent photoreactivity of imines based on the introduction of a donor–acceptor (D-A) structure to extend the lifetime of their photoexcited states. A series of spectroscopic analyses and density functional theory calculations reveal unique photophysical properties of the D-A-type imines. Furthermore, the reactivity of the D-A-type imines is demonstrated by using them as a photoredox catalyst for atom-transfer radical addition. These findings illuminate a previously neglected chemical space in the field of photochemistry, which will be exploited by taking advantage of the inherent structural modularity of imines.
• Redox-regulated divergence in photocatalytic addition of α-nitro alkyl radicals to styrenes

  Yuto Tsuchiya, Ryota Onai, Daisuke Uraguchi, Takashi Ooi

  Chemical Communications 2020
• Inserting Nitrogen: An Effective Concept To Create Nonplanar and Stimuli-Responsive Perylene Bisimide Analogues

  Sakiho Hayakawa, Ayumi Kawasaki, Yongseok Hong, Daisuke Uraguchi, Takashi Ooi, Dongho Kim, Tomoyuki Akutagawa, Norihito Fukui, Hiroshi Shinokubo

  Journal of the American Chemical Society 2019/12/18 [Refereed][Not invited]
  
• Formal Hydroformylation of α,β-Unsaturated Carboxylic Acids under Photoexcited Ketone Catalysis

  Kailong Zhu, Tsuyoshi Ohtani, Chandra Bhushan Tripathi, Daisuke Uraguchi, Takashi Ooi

  Chemistry Letters 48 (7) 715 - 717 0366-7022 2019/07/05
• Organic molecular catalysts in radical chemistry: Challenges toward selective transformations

  Daisuke Uraguchi, Kohsuke Ohmatsu, Takashi Ooi

  Molecular Technology: Materials Innovation 163 - 197 2019/02/06 

  This chapter focuses on the systems with catalytically relevant organic molecules, aiming at the progress in the development of radical-mediated selective transformations. The use of photochemical processes for the generation of radicals is an environmentally benign protocol, and organic chromophores are suitable candidates of a radical-generating subunit to act as an organic photocatalyst. Organic photocatalysis offers far more than "metal-free" alternatives to transition metal-catalyzed transformations. The leading challenges associated with chiral thiol-catalyzed stereoselective transformations have been reported by Roberts and coworker. Among the various organic molecular catalysts reported to date, chiral primary and secondary amines have found wide spread application since l-proline was employed as a chiral catalyst for asymmetric aldol reactions and other designer chiral amine catalysts were used for asymmetric Diels-Alder reactions. It is indisputable that sustainable chemical synthesis in the future requires straightforward and reliable processes to construct organic frameworks and in this context, radical reactions demonstrate considerable potential.
• Photocatalytic borylcyclopropanation of α-boryl styrenes

  Tsuyoshi Ohtani, Yuto Tsuchiya, Daisuke Uraguchi, Takashi Ooi

  Organic Chemistry Frontiers 2019
• A femtomolar-range suicide germination stimulant for the parasitic plant Striga hermonthica

  Daisuke Uraguchi, Keiko Kuwata, Yuh Hijikata, Rie Yamaguchi, Hanae Imaizumi, Sathiyanarayanan AM, Christin Rakers, Narumi Mori, Kohki Akiyama, Stephan Irle, Peter McCourt, Toshinori Kinoshita, Takashi Ooi, Yuichiro Tsuchiya

  Science 362 (6420) 1301 - 1305 2018/12/14
• Catalyst-Directed Guidance of Sulfur-Substituted Enediolates to Stereoselective Carbon–Carbon Bond Formation with Aldehydes

  Daisuke Uraguchi, Kohei Yamada, Makoto Sato, Takashi Ooi

  Journal of the American Chemical Society 140 (15) 5110 - 5117 1520-5126 2018/04/18 [Not refereed][Not invited]
   

  A highly chemo-, regio-, and stereoselective glycolate aldol reaction of sulfur-substituted enediolates with aldehydes was developed by employing a l-cyclohexylglycine-derived chiral iminophosphorane as a catalyst. The key for establishing this protocol is the distinct ability of the iminophosphorane catalyst to precisely direct the equilibrium mixture of the enediolates toward the intermolecular carbon-carbon bond formation with simultaneous yet rigorous control of relative and absolute stereochemistry. The critical importance of the cyclohexyl substituents on the catalyst backbone in dictating the reaction pathway and the stereochemical outcome was elucidated through an extensive quantum analysis by density functional theory calculations.
• Catalyst-Enabled Site-Divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors

  Daisuke Uraguchi, Ryo Shibazaki, Naoya Tanaka, Kohei Yamada, Ken Yoshioka, Takashi Ooi

  Angewandte Chemie 130 (17) 4822 - 4826 2018/04/16
• Catalyst-Enabled Site-Divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors

  Daisuke Uraguchi, Ryo Shibazaki, Naoya Tanaka, Kohei Yamada, Ken Yoshioka, Takashi Ooi

  Angewandte Chemie International Edition 57 (17) 4732 - 4736 1521-3773 2018/04/16 [Not refereed][Not invited]
   

  A site-divergent stereoselective Michael reaction system is developed based on the identification of two distinct catalysts. Cinchonidine-derived thiourea catalyzes the 1,4-addition of prochiral azlactone enolates to enynyl N-acyl pyrazoles in a highly diastereo- and enantioselective manner to give stereochemically defined alkynes, while P-spiro chiral triaminoiminophosphorane catalytically controls the stereoselective 1,6-addition and the consecutive γ-protonation of the vinylogous enolate intermediate to afford Z,E-configured conjugated dienes. This 1,6-adduct serves as a valuable precursor for the synthesis of a 2-amino-2-deoxy sugar.
• Allenedicarboxylate as a Stereochemically Labile Electrophile for Chiral Organic Base-catalyzed Stereoselective Michael Addition

  Daisuke Uraguchi, Yasutaka Kawai, Hitoshi Sasaki, Kohei Yamada, Takashi Ooi

  Chemistry Letters 47 (4) 594 - 597 0366-7022 2018/04/05 [Not refereed][Not invited]
   

  A highly stereoselective Michael addition of α-amino acidderived 2-benzyloxythiazol-5(4H)-ones to dimethyl allenedicarboxylate was developed by employing P-spiro chiral triaminoiminophosphorane bearing (S)-sec-butyl groups as a catalyst. Theoretical investigation of the transition-state models for the reaction and control experiments suggested the intervention of a dynamic kinetic resolution of the axially chiral allene acceptor. The synthetic utility of this method was demonstrated through the transformation of the stereochemically homogeneous Michael adduct to an α-vinylic α-amino acid derivative.
• Molecular Design, Synthesis, and Asymmetric Catalysis of a Hexacoordinated Chiral Phosphate Ion

  Daisuke Uraguchi, Hitoshi Sasaki, Yuto Kimura, Takaki Ito, Takashi Ooi

  Journal of the American Chemical Society 140 (8) 2765 - 2768 1520-5126 2018/02/28 [Not refereed][Not invited]
   

  We describe the design, synthesis, and characterization of a chiral hexacoordinated phosphate ion that features an octahedral P(V) core consisting of two N,N,O-tridentate backbones. We further demonstrate that the corresponding hydrogen phosphate acts as an effective catalyst for a highly enantioselective Pictet-Spengler-type reaction, wherein the relationship between the structure of the chiral phosphate ion and its ability to dictate the absolute stereochemistry is revealed in conjunction with precise structural elucidation of the phosphate ion.
• [5.5]-P-Spirocyclic Chiral Triaminoiminophosphorane-Catalyzed Asymmetric Hydrophosphonylation of Aldehydes and Ynones

  Daisuke Uraguchi, Takaki Ito, Yuto Kimura, Yumiko Nobori, Makoto Sato, Takashi Ooi

  Bulletin of the Chemical Society of Japan 90 (5) 546 - 555 0009-2673 2017/05/15 [Refereed][Not invited]
   

  Development of highly efficient and enantioselective hydrophosphonylations of aldehydes and ynones mediated by [5.5]P-spirocyclic chiral triaminoiminophosphoranes as base catalysts is described. The strong basicity of the iminophosphoranes and hydrogen-bond donating ability of their conjugate acids, tetraaminophosphonium ions, are critical for the facile generation of aminophosphonium phosphites with substantial nucleophilicity as well as for the subsequent selective, yet productive, P-C bond formation by suppressing undesired side reactions. The scope and limitations of these catalytic asymmetric methodologies are also reported.
• Acridinium Betaine as a Single-Electron-Transfer Catalyst: Design and Application to Dimerization of Oxindoles

  Daisuke Uraguchi, Masahiro Torii, Takashi Ooi

  ACS Catalysis 7 (4) 2765 - 2769 2155-5435 2017/04/07 [Refereed][Not invited]
   

  An intramolecular ion-pairing acridinium phenoxide possessing a redox-active component and a basic site within a single molecular framework is developed. The potential of the acridinium betaine as a chemical redox catalyst is demonstrated by its application to the homodimerization of 3-aryl oxindoles, which proceeds through proton-coupled electron-transfer pathway. Analysis of the kinetic profile has provided important clues to understand the reaction mechanism.
• Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst

  Daisuke Uraguchi, Ken Yoshioka, Takashi Ooi

  Nature Communications 8 (1) 14793  2041-1723 2017/04 [Refereed][Not invited]
   

  Catalytic systems that allow selective generation of any diastereomer of a reaction product bearing multiple stereocentres through minimal modification of a single catalyst scaffold remain elusive, particularly for carbon-carbon bond formations requiring simultaneous control of multiple selectivity factors. Here, we report a catalyst-directed pinpoint inversion of diastereochemical preference in the 1,6-addition of azlactones to d-aryl dienyl carbonyl compounds with full control over other selectivities preserved. This rigorous diastereodivergence is enabled by the slight structural adjustment of a chiral iminophosphorane catalyst, providing access to all the stereoisomers with high regio-, distereo- and enantioselectivity. The utility of this method is demonstrated in the facile stereodivergent preparation of densely functionalized proline derivatives. The experimental and computational elucidation of the origin of the diastereodivergence is also reported.
• Correction to: Generation of chiral phosphonium dialkyl phosphite as a highly reactive p-nucleophile: Application to asymmetric hydrophosphonylation of aldehydes (J. Am. Chem. Soc. (2009) 131 (3836−3837) DOI: 10.1021/ja810043d)

  Daisuke Uraguchi, Takaki Ito, Takashi Ooi

  Journal of the American Chemical Society 131 (11) X3836 - 3837 0002-7863 2017/03/01 [Refereed][Not invited]
  
• Correction to "Generation of Chiral Phosphonium Dialkyl Phosphite as a Highly Reactive P-Nucleophile: Application to Asymmetric Hydrophosphonylation of Aldehydes"

  Daisuke Uraguchi, Takaki Ito, Takashi Ooi

  JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 139 (8) 3299 - 3299 0002-7863 2017/03 [Refereed][Not invited]
  
• Origin of High Regio-, Diastereo-, and Enantioselectivities in 1,6-Addition of Azlactones to Dienyl N-Acylpyrroles: A Computational Study

  Masahiro Yamanaka, Ken Sakata, Ken Yoshioka, Daisuke Uraguchi, Takashi Ooi

  The Journal of Organic Chemistry 82 (1) 541 - 548 0022-3263 2017/01/06 [Refereed][Not invited]
   

  Chiral P-spiro triaminoiminophosphorane (1) was developed to promote the highly regio-, diastereo-, and enantioselective 1,6- and 1,8-additions of azlactones (2 center dot H) to dienyl and trienyl N-acylpyrroles (3 and 4). DFT calculations enabled us to gain deep insight into the whole reaction mechanism as well as the origin of the high regio- and stereoselectivities. The present reaction consists of three steps: (1) formation of the phosphonium-enolate ion-pair complex by deprotonation of 2 center dot H with 1, (2) C-C bond formation of 2 with 3 and 4, and (3) protonation of the resulting enolate anion. The C-C bond formation is irreversible, and the rate- and stereodetermining step. The C-gamma-protonation preferentially proceeds rather than the thermodynamically and kinetically disfavored O- and C-alpha-protonation, respectively. The high regio- and enantioselectivities are mainly attributed to the steric and electronic features of 1 center dot H and 3/4. The hydrogen bonds (NH-O and CH-O) and the attractive CH-pi interaction between 1 center dot H and 2 and 3 play a key role in achieving high stereocontrol. The high regioselectivity is mainly controlled by the structural distortion of 1 center dot H and the disruption of the p-conjugated system of 3 (1,4-system) and 4 (1,4- and 1,6-systems).
• Stereoselective Aza-Henry Reaction of 3-Nitro-dihydro-2(1H)-quinolones with N-Boc-Aldimines under the Catalysis of Chiral Ammonium Betaines

  Takashi Ooi, Daisuke Uraguchi, Masahiro Torii, Kohsuke Kato

  HETEROCYCLES 94 (3) 441 - 441 0385-5414 2017 [Refereed][Not invited]
   

  A highly enantioselective aza-Henry reaction between 3-nitro-dihydro-2(1H)-quinolones and N-Boc-aldimines was developed by using a chiral ammonium betaine as a catalyst. This protocol provides a direct synthetic method for accessing hydroquinoline derivatives possessing a tetrasubstituted stereogenic center at the C3 position and casts light on the utility of the a-functionalization of dihydroquinolones.
• Unique site-selectivity control in asymmetric Michael addition of azlactone to alkenyl dienyl ketones enabled by P-spiro chiral iminophosphorane catalysis

  Ken Yoshioka, Kohei Yamada, Daisuke Uraguchi, Takashi Ooi

  Chemical Communications 53 (40) 5495 - 5498 1359-7345 2017 [Not refereed][Not invited]
   

  Simultaneous recognition of distance and direction of conjugation from carbonyl in alkenyl dienyl ketones enables a highly site-selective asymmetric 1,6-addition.

• N-Sulfonyl α-imino ester-derived chiral oxaziridines: catalytic asymmetric synthesis and application as a modular chiral organic oxidant

  Naoya Tanaka, Ryosuke Tsutsumi, Daisuke Uraguchi, Takashi Ooi

  Chemical Communications 53 (52) 6999 - 7002 1359-7345 2017 [Refereed][Not invited]
   

  A novel class of chiral N-sulfonyl oxaziridines is catalytically prepared and introduced for use as highly reactive and enantiospecific oxidants.

• Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles

  Masahiro Torii, Kohsuke Kato, Daisuke Uraguchi, Takashi Ooi

  Beilstein Journal of Organic Chemistry 12 2099 - 2103 1860-5397 2016/09/28 [Refereed][Invited]
   

  A highly diastereo- and enantioselective Mannich-type reaction of 3-aryloxindoles with N-Boc aldimines was achieved under the catalysis of axially chiral ammonium betaines. This catalytic method provides a new tool for the construction of consecutive quaternary and tertiary stereogenic carbon centers on biologically intriguing molecular frameworks with high fidelity.
• Independence from the Sequence of Single-Electron Transfer of Photoredox Process in Redox-Neutral Asymmetric Bond-Forming Reaction

  Tomohito Kizu, Daisuke Uraguchi, Takashi Ooi

  The Journal of Organic Chemistry 81 (16) 6953 - 6958 0022-3263 2016/08/19 [Refereed][Not invited]
   

  A catalytic cycle initiated by the oxidative quenching of the excited photosensitizer (Ir*(ppy)(3)) is established for the enantioselective coupling between (N-arylamino)methanes and (N-methanesulfonyl)-aldimines catalyzed by Ir-based photosensitizer and a Chiral (arylamino)-phosphonium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate under visible light irradiation. This achievement clearly demonstrates the insensitivity of this redox-neutral asymmetric reaction to the sequence of the key redox, events involved in the synergistic catalysis.
• Site-Selective Conjugate Addition Through Catalytic Generation of Ion-Pairing Intermediates

  Daisuke Uraguchi, Takashi Ooi

  SITE-SELECTIVE CATALYSIS 372 55 - 83 0340-1022 2016 [Refereed][Not invited]
   

  Site-selectivity in conjugate addition reactions is tightly associated with the principle of vinylogy. Various vinylogous nucleophiles and electrophiles have been applied to stereoselective conjugate additions directed by chiral small-molecule catalysts. This chapter focuses on the systems that control site- and stereoselectivity via chiral ion-pairing intermediates under organocatalytic conditions and describes individual vinylogous substrates in a separate section. Although site-selectivity originates largely from the intrinsic stereoelectronic nature of individual substrates, catalyst-controlled site-selectivity can be attained in certain cases.
• Fenton reagent-catalyzed trifluoromethylation of enamines of 3-oxocarboxylates with CF3I

  Yuhki Ohtsuka, Daisuke Uraguchi, Kyoko Yamamoto, Kenji Tokuhisa, Tetsu Yamakawa

  Journal of Fluorine Chemistry 181 1 - 6 0022-1139 2016/01 [Refereed][Not invited]
   

  The trifluoromethylation of enamines of ethyl 3-oxocarboxylates catalyzed by Fenton reagent with CF3I was investigated. Trifluoromethylation followed by acid hydrolysis provided 3-oxo-2-(trifluoromethyl)-carboxylates in 64-94% yields, which were greater than those obtained by the trifluoromethylation of 3-oxocarboxylates as reported previously. Enamines trifluoromethylated at the 2-position were isolated as intermediates. Hydrolysis and successive decarboxylation of the obtained 3-oxo-2-(trifluoromethyl)-carboxylates under acidic conditions provided (2,2,2-trifluoroethyl)ketones in satisfactory yields. (C) 2015 Elsevier B.V. All rights reserved.
• Synergistic Catalysis of Ionic Brønsted Acid and Photosensitizer for a Redox Neutral Asymmetric α-Coupling of N-Arylaminomethanes with Aldimines

  Daisuke Uraguchi, Natsuko Kinoshita, Tomohito Kizu, Takashi Ooi

  Journal of the American Chemical Society 137 (43) 13768 - 13771 0002-7863 2015/11/04 [Refereed][Not invited]
   

  A redox neutral, highly enantioselective coupling between N-arylaminomethanes and N-sulfonyl aldimines was developed by harnessing the efficient catalysis of P-spiro chiral arylaminophosphonium barfate and a transition-metal photosensitizer under visible light irradiation. This mode of synergistic catalysis provides a powerful strategy for controlling the bond-forming processes of reactive radical intermediates.
• HighlyE-Selective and Enantioselective Michael Addition to Electron-Deficient Internal Alkynes Under Chiral Iminophosphorane Catalysis

  Daisuke Uraguchi, Kohei Yamada, Takashi Ooi

  Angewandte Chemie International Edition 54 (34) 9954 - 9957 1433-7851 2015/08/17 [Refereed][Not invited]
   

  A highly E-selective and enantioselective conjugate addition of 2-benzyloxythiazol-5(4H)-ones to beta-substituted alkynyl N-acyl pyrazoles is achieved under the catalysis of a P-spiro chiral iminophosphorane. Simultaneous control of the newly generated central chirality and olefin geometry is possible with a wide array of the alkynyl Michael acceptors possessing different aromatic and aliphatic beta-substituents, as well as the various alpha-amino acid-derived thiazolone nucleophiles. This protocol provides access to structurally diverse, optically active alpha-amino acids bearing a geometrically defined trisubstituted olefinic component at the alpha-position.
• Chiral Ammonium Betaine-Catalyzed Highly Stereoselective Aza-Henry Reaction of α-Aryl Nitromethanes with AromaticN-Boc Imines

  Daisuke Uraguchi, Keigo Oyaizu, Haruhiro Noguchi, Takashi Ooi

  Chemistry - An Asian Journal 10 (2) 334 - 337 1861-4728 2015/02
• Vinylogy in nitronates: utilization of alpha-aryl conjugated nitroolefins as a nucleophile for a highly stereoselective aza-Henry reaction

  Keigo Oyaizu, Daisuke Uraguchi, Takashi Ooi

  CHEMICAL COMMUNICATIONS 51 (21) 4437 - 4439 1359-7345 2015 

  The vinylogous reactivity of alpha,beta-disubstituted nitroolefins was uncovered through the facile generation of the corresponding alpha-substituted vinylogous nitronates and their use in the development of a highly diastereo-and enantioselective aza-Henry reaction with N-Boc aldimines under the catalysis of chiral ammonium betaines. The novel vinylogous nitronates undergo stereoselective bond formation at the sterically encumbered alpha-position exclusively, allowing the construction of contiguous tertiary-quaternary stereogenic carbon centers.
• Enantioselective reductive multicomponent coupling reactions between isatins and aldehydes

  Matthew A. Horwitz, Naoya Tanaka, Takuya Yokosaka, Daisuke Uraguchi, Jeffrey S. Johnson, Takashi Ooi

  Chemical Science 6 (11) 6086 - 6090 2041-6520 2015 [Refereed][Not invited]
   

  A reductive coupling of two different carbonyls via a polar two-electron reaction mechanism was developed and the stereochemical outcome of this multicomponent process is precisely controlled by a chiral triaminoiminophosphorane.

• The Practical Preparation of Chiral N-Sulfonyl Oxaziridines via Catalytic Asymmetric Payne Oxidation

  Takashi Ooi, Ryosuke Tsutsumi, Seonwoo Kim, Daisuke Uraguchi

  Synthesis 46 (07) 871 - 878 0039-7881 2014/02/21
• Catalytic asymmetric Payne oxidation under the catalysis of P-spiro chiral triaminoiminophosphorane: application to the synthesis of N-sulfonyl oxaziridines

  Daisuke Uraguchi, Ryosuke Tsutsumi, Takashi Ooi

  Tetrahedron 70 (8) 1691 - 1701 0040-4020 2014/02
• Enantioselective formal α-allylation of nitroalkanes through a chiral iminophosphorane-catalyzed Michael reaction–Julia–Kocienski olefination sequence

  Daisuke Uraguchi, Shinji Nakamura, Hitoshi Sasaki, Yuki Konakade, Takashi Ooi

  Chem. Commun. 50 (26) 3491 - 3493 1359-7345 2014 

  A chiral iminophosphorane-catalyzed Michael addition–Julia–Kocienski olefination sequence for the asymmetric formal α-allylation of nitroalkanes is developed.

• Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Brønsted acid catalysis

  Daisuke Uraguchi, Tomohito Kizu, Yuki Ohira, Takashi Ooi

  Chem. Commun. 50 (88) 13489 - 13491 1359-7345 2014 

  P-Spiro chiral diaminodioxaphosphonium ion discriminates the enantiofaces of α-halo and alkoxy carboxylic acid-derived ketene disilyl acetals by the recognition of the electronic difference between two substituents of the ketene disilyl acetal in the proton-transfer event.

• Chiral C2 Catalysts

  Daisuke Uraguchi, Kohsuke Ohmatsu, Takashi Ooi

  Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications 1-3 161 - 193 2013/08/23 [Refereed][Not invited]
  
• Catalytic Asymmetric Oxidation of N-Sulfonyl Imines with Hydrogen Peroxide–Trichloroacetonitrile System

  Daisuke Uraguchi, Ryosuke Tsutsumi, Takashi Ooi

  Journal of the American Chemical Society 135 (22) 8161 - 8164 0002-7863 2013/06/05 [Refereed][Not invited]
   

  An efficient and highly enantioselective Payne-type oxidation of N-sulfonyl imines is developed. The reaction exhibits broad substrate generality and unique chemoselectivity based on the combined use of hydrogen peroxide and trichloroacetonitrile under the catalysis of P-spiro chiral triaminoiminophosphorane.
• Highly stereoselective Michael addition of azlactones to electron-deficient triple bonds under P-spiro chiral iminophosphorane catalysis: importance of protonation pathway

  Daisuke Uraguchi, Yusuke Ueki, Atsushi Sugiyama, Takashi Ooi

  Chemical Science 4 (3) 1308 - 1308 2041-6520 2013
• Nitroolefins as a Nucleophilic Component for Highly Stereoselective Aza Henry Reaction under the Catalysis of Chiral Ammonium Betaines

  Daisuke Uraguchi, Keigo Oyaizu, Takashi Ooi

  Chemistry - A European Journal 18 (27) 8306 - 8309 0947-6539 2012/07/02
• Base-Catalyzed Direct Aldolization of α-Alkyl-α-Hydroxy Trialkyl Phosphonoacetates

  Michael T. Corbett, Daisuke Uraguchi, Takashi Ooi, Jeffrey S. Johnson

  Angewandte Chemie International Edition 51 (19) 4685 - 4689 1433-7851 2012/05/07
• Ionic Nucleophilic Catalysis of Chiral Ammonium Betaines for Highly Stereoselective Aldol Reaction from Oxindole-Derived Vinylic Carbonates

  Daisuke Uraguchi, Kyohei Koshimoto, Takashi Ooi

  Journal of the American Chemical Society 134 (16) 6972 - 6975 0002-7863 2012/04/25
• Syntheses of 2-(trifluoromethyl)-1,3-dicarbonyl compounds through direct trifluoromethylation with CF3I and their application to fluorinated pyrazoles syntheses

  Yuhki Ohtsuka, Daisuke Uraguchi, Kyoko Yamamoto, Kenji Tokuhisa, Tetsu Yamakawa

  Tetrahedron 68 (12) 2636 - 2649 0040-4020 2012/03
• Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins

  Daisuke Uraguchi, Yusuke Ueki, Takashi Ooi

  Chem. Sci. 3 (3) 842 - 845 2041-6520 2012
• Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins

  Daisuke Uraguchi, Natsuko Kinoshita, Daisuke Nakashima, Takashi Ooi

  Chemical Science 3 (11) 3161 - 3161 2041-6520 2012
• Enantioselective Aza-Michael Addition to Conjugated Nitroenynes Catalyzed by Chiral Arylaminophosphonium Barfates

  Takashi Ooi, Daisuke Uraguchi, Natsuko Kinoshita, Tomohito Kizu

  Synlett 2011 (09) 1265 - 1267 0936-5214 2011/06
• Controlled Assembly of Chiral Tetraaminophosphonium Aryloxide-Arylhydroxide(s) in Solution

  Daisuke Uraguchi, Yusuke Ueki, Takashi Ooi

  Angewandte Chemie International Edition 50 (16) 3681 - 3683 1433-7851 2011/04/11
• Catalytic Asymmetric Protonation of α-Amino Acid-Derived Ketene Disilyl Acetals Using P-Spiro Diaminodioxaphosphonium Barfates as Chiral Proton

  Daisuke Uraguchi, Natsuko Kinoshita, Takashi Ooi

  Journal of the American Chemical Society 132 (35) 12240 - 12242 0002-7863 2010/09/08
• Catalytic Asymmetric Direct Henry Reaction of Ynals: Short Syntheses of (2S,3R)-(+)-Xestoaminol C and (−)-Codonopsinines

  Daisuke Uraguchi, Shinji Nakamura, Takashi Ooi

  Angewandte Chemie International Edition 49 (41) 7562 - 7565 1433-7851 2010/08/31
• Chiral Ammonium Betaines as Ionic Nucleophilic Catalysts

  Daisuke Uraguchi, Kyohei Koshimoto, Shuhei Miyake, Takashi Ooi

  Angewandte Chemie International Edition 49 (32) 5567 - 5569 1433-7851 2010/07/07
• Performance of C1-symmetric chiral ammonium betaines as catalysts for the enantioselective Mannich-type reaction of α-nitrocarboxylates

  Daisuke Uraguchi, Kyohei Koshimoto, Chisato Sanada, Takashi Ooi

  Tetrahedron: Asymmetry 21 (9-10) 1189 - 1190 0957-4166 2010/05
• Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide

  Tatsuhito Kino, Yu Nagase, Yuhki Ohtsuka, Kyoko Yamamoto, Daisuke Uraguchi, Kenji Tokuhisa, Tetsu Yamakawa

  Journal of Fluorine Chemistry 131 (1) 98 - 105 0022-1139 2010/01
• Flexible synthesis, structural determination, and synthetic application of a new C1-symmetric chiral ammonium betaine

  Daisuke Uraguchi, Kyohei Koshimoto, Takashi Ooi

  Chem. Commun. 46 (2) 300 - 302 1359-7345 2010
• Catalytic asymmetric hydrophosphonylation of ynones

  Daisuke Uraguchi, Takaki Ito, Shinji Nakamura, Takashi Ooi

  Chemical Science 1 (4) 488 - 488 2041-6520 2010
• Diastereo- and Enantioselective Direct Henry Reaction of Pyruvates Mediated by Chiral P-Spiro Tetraaminophosphonium Salts

  Daisuke Uraguchi, Takaki Ito, Shinji Nakamura, Sawako Sakaki, Takashi Ooi

  Chemistry Letters 38 (11) 1052 - 1053 0366-7022 2009/11/05
• Chiral Organic Ion Pair Catalysts Assembled Through a Hydrogen-Bonding Network

  Daisuke Uraguchi, Yusuke Ueki, Takashi Ooi

  SCIENCE 326 (5949) 120 - 123 0036-8075 2009/10 

  Research to develop structurally discrete, chiral supramolecular catalysts for asymmetric organic transformations has met with limited success. Here, we report that a chiral tetraaminophosphonium cation, two phenols, and a phenoxide anion appear to self-assemble into a catalytically active supramolecular architecture through intermolecular hydrogen bonding. The structure of the resulting molecular assembly was determined in the solid state by means of x-ray diffraction analysis. Furthermore, in solution the complex promotes a highly stereoselective conjugate addition of acyl anion equivalents to alpha,beta-unsaturated ester surrogates with a broad substrate scope. All structural components of the catalyst cooperatively participate in the stereocontrolling event.
• Cp2Ni-KOt-Bu-BEt3 (or PPh3) Catalyst System for Direct C−H Arylation of Benzene, Naphthalene, and Pyridine

  Osamu Kobayashi, Daisuke Uraguchi, Tetsu Yamakawa

  Organic Letters 11 (12) 2679 - 2682 1523-7060 2009/06/18
• Chiral Arylaminophosphonium Barfates as a New Class of Charged Brønsted Acid for the Enantioselective Activation of Nonionic Lewis Bases

  Daisuke Uraguchi, Daisuke Nakashima, Takashi Ooi

  Journal of the American Chemical Society 131 (21) 7242 - 7243 0002-7863 2009/06/03
• Synthesis of α-trifluoromethylstyrene derivatives via Ni-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and aryl Grignard reagents

  Osamu Kobayashi, Daisuke Uraguchi, Tetsu Yamakawa

  Journal of Fluorine Chemistry 130 (6) 591 - 594 0022-1139 2009/06
• Synthesis of α-trifluoromethylstyrene derivatives via Pd-catalyzed cross-coupling of 2-bromo-3,3,3-trifluoropropene and arylmagnesium bromides

  Osamu Kobayashi, Daisuke Uraguchi, Tetsu Yamakawa

  Journal of Molecular Catalysis A: Chemical 302 (1-2) 7 - 10 1381-1169 2009/04
• Generation of Chiral Phosphonium Dialkyl Phosphite as a Highly Reactive P-Nucleophile: Application to Asymmetric Hydrophosphonylation of Aldehydes

  Daisuke Uraguchi, Takaki Ito, Takashi Ooi

  Journal of the American Chemical Society 131 (11) 3836 - 3837 0002-7863 2009/03/25
• Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids via Enantioselective Alkylation of Azlactones under Biphasic Conditions Using P-Spiro Chiral Tetraaminophosphonium Salts as a Phase-Transfer Catalyst

  Takashi Ooi, Daisuke Uraguchi, Yoshihiro Asai, Yuki Seto

  Synlett 2009 (04) 658 - 660 0936-5214 2009/03
• Site-Directed Asymmetric Quaternization of a Peptide Backbone at a C-Terminal Azlactone

  Daisuke Uraguchi, Yoshihiro Asai, Takashi Ooi

  Angewandte Chemie International Edition 48 (4) 733 - 737 1433-7851 2009/01/12
• Chiral Tetraaminophosphonium Carboxylate-Catalyzed Direct Mannich-Type Reaction

  Daisuke Uraguchi, Yusuke Ueki, Takashi Ooi

  Journal of the American Chemical Society 130 (43) 14088 - 14089 0002-7863 2008/10/29
• Chiral Ammonium Betaines: A Bifunctional Organic Base Catalyst for Asymmetric Mannich-Type Reaction of α-Nitrocarboxylates

  Daisuke Uraguchi, Kyohei Koshimoto, Takashi Ooi

  Journal of the American Chemical Society 130 (33) 10878 - 10879 0002-7863 2008/08/01
• Catalytic trifluoromethylation of uracil to 5-trifluoromethyluracil by use of CF3I and its industrial applications

  Daisuke Uraguchi, Kyoko Yamamoto, Yuhki Ohtsuka, Kenji Tokuhisa, Tetsu Yamakawa

  Applied Catalysis A: General 342 (1-2) 137 - 143 0926-860X 2008/06
• Synthesis of Chiral Tetraaminophosphonium Chlorides from N-Boc a-Amino Acid Esters

  Takashi Ooi, Daisuke Uraguchi, Sawako Sakaki, Yusuke Ueki, Takaki Ito

  HETEROCYCLES 76 (2) 1081 - 1081 0385-5414 2008
• Chiral Tetraaminophosphonium Salt-Mediated Asymmetric Direct Henry Reaction

  Daisuke Uraguchi, Sawako Sakaki, Takashi Ooi

  Journal of the American Chemical Society 129 (41) 12392 - 12393 0002-7863 2007/10
• Chiral phosphoric acid-catalyzed enantioselective Aza-Friedel-Crafts reaction of Indoles

  Masahiro Terada, Shigeko Yokoyama, Keiichi Sorimachi, Daisuke Uraguchi

  ADVANCED SYNTHESIS & CATALYSIS 349 (11-12) 1863 - 1867 1615-4150 2007/08 

  A highly enantioselective 1,2-aza-Friedel-Crafts reaction of N-tert-butyldimethylsilylindole with N-tert-butoxycarbonyl aromatic imines is demonstrated using a BINOL-derived monophosphoric acid catalyst. The present approach provides efficient access to 3-indolylmethaneamines with aryl substituents in excellent enantioselectivities (up to 98 % ee). An inversion in the sense of enantioselection was found between monophosphoric acid catalysts bearing different substituents introduced at the 3,3'-position of binaphthyl backbone. We also calculated the three-dimensional structure of the monophosphoric acid catalysts to speculate on the inversion of the stereochemical outcome.
• Efficient synthetic protocol for substituted guanidines via copper(I)-mediated intermolecular amination of isothiourea derivatives

  Hitoshi Ube, Daisuke Uraguchi, Masahiro Terada

  Journal of Organometallic Chemistry 692 (1-3) 545 - 549 0022-328X 2007/01/01 

  Amination of S-methyl-N,N′-bis-Boc-isothiourea with either primary or sterically hindered secondary amines promoted by copper(I) chloride and K2CO3 gave N,N′-bis-Boc protected guanidines in good to excellent yields under mild reaction conditions. © 2006 Elsevier B.V. All rights reserved.
• Phosphorodiamidic Acid as a Novel Structural Motif of Brønsted Acid Catalysts for Direct Mannich Reaction ofN-Acyl Imines with 1,3-Dicarbonyl Compounds

  Masahiro Terada, Keiichi Sorimachi, Daisuke Uraguchi

  Synlett (1) 0133 - 0136 0936-5214 2006
• Organocatalytic Asymmetric Direct Alkylation of α-Diazoester via C−H Bond Cleavage

  Daisuke Uraguchi, Keiichi Sorimachi, Masahiro Terada

  Journal of the American Chemical Society 127 (26) 9360 - 9361 0002-7863 2005/07
• Stereodivergent Construction of Cyclic Ethers by a Regioselective and Enantiospecific Rhodium-Catalyzed Allylic Etherification: Total Synthesis of Gaur Acid

  P. Andrew Evans, David K. Leahy, William J. Andrews, Daisuke Uraguchi

  Angewandte Chemie International Edition 43 (36) 4788 - 4791 1433-7851 2004/09/13 [Refereed][Not invited]
  
• Organocatalytic Asymmetric Aza-Friedel−Crafts Alkylation of Furan

  Daisuke Uraguchi, Keiichi Sorimachi, Masahiro Terada

  Journal of the American Chemical Society 126 (38) 11804 - 11805 0002-7863 2004/09
• Efficient asymmetric catalysis of chiral organoaluminum complex for enantioselective ene reactions of aldehydes

  Takashi Ooi, Kohsuke Ohmatsu, Daisuke Uraguchi, Keiji Maruoka

  Tetrahedron Letters 45 (23) 4481 - 4484 0040-4039 2004/05
• Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation

  Daisuke Uraguchi, Masahiro Terada

  Journal of the American Chemical Society 126 (17) 5356 - 5357 0002-7863 2004/05
• Catalytic Asymmetric Allylation of Aldehydes and Related Reactions with Bis(((S)-binaphthoxy)(isopropoxy)titanium) Oxide as aμ-Oxo-Type Chiral Lewis Acid

  Hideo Hanawa, Daisuke Uraguchi, Shunsuke Konishi, Takuya Hashimoto, Keiji Maruoka

  Chemistry - A European Journal 9 (18) 4405 - 4413 0947-6539 2003/09/22
• Regio- and Enantiospecific Rhodium-Catalyzed Arylation of Unsymmetrical Fluorinated Acyclic Allylic Carbonates:  Inversion of Absolute Configuration

  P. Andrew Evans, Daisuke Uraguchi

  Journal of the American Chemical Society 125 (24) 7158 - 7159 0002-7863 2003/06
• Unique Synthetic Utility of BF3·OEt2in the Highly Diastereoselective Reduction of Hydroxy Carbonyl and Dicarbonyl Substrates

  Takashi Ooi, Daisuke Uraguchi, Junko Morikawa, Keiji Maruoka

  Organic Letters 2 (14) 2015 - 2017 1523-7060 2000/07
• Chemistry of chelate-type hypervalent boron and aluminum: Utilization for selective organic synthesis

  Uraguchi D, Ooi T, Maruoka K

  JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN The Society of Synthetic Organic Chemistry, Japan 58 (1) 14 - 22 0037-9980 2000/01 [Refereed][Not invited]
   

  In this review, the hypercoordination of boron and aluminum as typical main group elements is embodied, and their synthetic utility is demonstrated with several synthetic examples. B and Al Lewis acids are found to be successfully utilized in several chelation-controlled reactions of various substrates (alkoxy carbonyl compounds, fluoro carbonyl compounds, fluoro epoxides, and alkoxy epoxides) via unprecedented pentacoordinate chelate-type complex formation by taking advantage of the exceedingly high affinity of B and Al to fluorine and oxygen, and hence, contrary to the previous observations, can be classified as chelating Lewis acid reagents rather than non-chelating Lewis acids. In addition to the experimental demonstration, such pentacoordinate complex formation of B and Al Lewis acids with various bidentate substrates is also characterized by low-temperature ¹H, ¹³c, ¹¹B, ²⁷AlNMR spectroscopy.
• Hypercoordination of aluminum: Evidence for the implication of pentacoordinate complexes in the R2AlCl-promoted reduction of alkoxycarbonyl substrates

  Takashi Ooi, Junko Morikawa, Daisuke Uraguchi, Keiji Maruoka

  Tetrahedron Letters 40 (15) 2993 - 2996 0040-4039 1999/04
• Pentacoordinate vs. Tetracoordinate complexation for alkoxycarbonyl compounds with dialkylboron triflates and trifluoroacetates ?

  Takashi Ooi, Daisuke Uraguchi, Keiji Maruoka

  Tetrahedron Letters 39 (44) 8105 - 8108 0040-4039 1998/10
• Organoaluminum-promoted selective addition to fluorinated carbonyl compounds via pentacoordinate trialkylaluminum complexes

  Takashi Ooi, Naoko Kagoshima, Daisuke Uraguchi, Keiji Maruoka

  Tetrahedron Letters 39 (39) 7105 - 7108 0040-4039 1998/09
• Hypercoordination of Boron and Aluminum:  Synthetic Utility as Chelating Lewis Acids

  Takashi Ooi, Daisuke Uraguchi, Naoko Kagoshima, Keiji Maruoka

  Journal of the American Chemical Society 120 (21) 5327 - 5328 0002-7863 1998/06
• Organoaluminum-catalyzed new alkylation of tert-alkyl fluorides: Synthetic utility of AlF interaction

  Takashi Ooi, Daisuke Uraguchi, Naoko Kagashima, Keiji Maruoka

  Tetrahedron Letters 38 (32) 5679 - 5682 0040-4039 1997/08

MISC

• スライムの進化先は有機触媒！？

  趙 強, 浦口 大輔  月刊化学  77-  (2)  2022/02  [Not refereed][Invited]
  
• Believe in the Power of Molecules

  Daisuke Uraguchi  Journal of Synthetic Organic Chemistry, Japan  79-  (7)  696  -698  2021/07/01
• Catalysis of Chiral Iminophosphorane for Simultaneous Control of Multiple Selectivity: Experimental and Theoretical Investigation

  Daisuke Uraguchi, Takashi Ooi  Journal of Synthetic Organic Chemistry, Japan  79-  (5)  406  -416  2021/05/01
• 人工ストリゴラクトンの設計

  土屋 雄一朗, 浦口 大輔, 大井 貴史  植物の生長調節  54-  (1)  49  -53  2019/06  [Refereed]
  
• Chemistry of Ammonium Betaines: Application to Ion-Pair Catalysis for Selective Organic Transformations

  Uraguchi, Daisuke, Ooi, Takashi  J. Synth. Org. Chem. Jpn.  76-  (11)  1144-1153  2018/11/09  [Refereed][Invited]
  
• 有機イオン対の触媒化学：構造に由来する機能発現

  浦口 大輔, 大松 亨介, 大井 貴史  ケミカルタイムズ  2018-  (2)  19-25  2018/04  [Not refereed][Invited]
  
• Trichloroperoxyacetamidic Acid

  Robert D Bach, Ryosuke Tsutsumi, Daisuke Uraguchi, Takashi Ooi  Encyclopedia of Reagents for Organic Synthesis  2018/03  [Not refereed][Invited]
  
• 有機分子触媒の化学－「輪」をもって尊しとなす－

  浦口 大輔, 大井 貴史  現代化学  558-  (9)  52-56  2017/08/18  [Not refereed][Invited]
  
• [5.5]-P-スピロ型キラルテトラアミノホスホニウム塩を用いる触媒的分子変換

  浦口 大輔, 大井 貴史  Wako Organic Square  59-  (3)  2-5  2017/03  [Not refereed][Invited]
  
• Lecture Tour upon Receiving the 10^th Lectureship Award MBLA

  Daisuke Uraguchi  Journal of Synthetic Organic Chemistry, Japan  73-  (6)  653  -662  2015
• 忘れられた反応剤Davis’オキサジリジン －不斉有機合成における最近の動向

  堤亮祐, 浦口大輔, 大井貴史  化学  63-  (10)  72-73  2013/10  [Not refereed][Invited]
  
• Development of P-Spiro Chiral Aminophosphonium Salts as a New Class of Versatile Organic Molecular Catalyst

  Daisuke Uraguchi, Takashi Ooi  JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN  68-  (11)  1185  -1194  2010/11  [Refereed][Not invited]
   

  A series of P-spiro chiral tetraaminophosphonium salts have been designed and synthesized as a new class of organic molecular catalysts, and their inherent abilities to exert four different, synthetically relevant asymmetric catalyses have been brought out through the unique molecular design on a single core structure, N4P+. Further, these catalyses have been applied to the development of various C-C, C-P, and C-N bond-forming reactions, in which the remarkably high catalytic performances and stereocontrolling abilities of the chiral tetraaminophosphonium salts have been successfully demonstrated.
• Development of D2-symmetric chiral tetraaminophosphonium salts as a catalyst for asymmetric phase-transfer reactions

  浦口 大輔, 大井 貴史  Fine chemicals  39-  (8)  42-48  -48  2010  [Not refereed][Invited]
  
• 水素結合供与型キラルホスホニウム/有機アニオンが示す新たなイオン「対」触媒作用

  上木 佑介, 浦口 大輔, 大井 貴史  触媒  52-  509-514  2010  [Refereed][Invited]
  
• P-スピロ型テトラアミノホスホニウム塩の創製と有機分子触媒としての機能発現

  浦口大輔  触媒  50-  683-687  2008  [Not refereed][Invited]
  
• 光学活性な炭素の三角形を作る―Corey-Chaykovsky反応と親電子剤活性化法の組み合わせ

  浦口 大輔, 大井 貴史  化学  63-  66-67  2008  [Not refereed][Not invited]
  
• Fe (II)-catalyzed trifluoromethylation of uracil derivatives with CF_3I

  URAGUCHI Daisuke, YAMAMOTO Kyoko, TOKUHISA Kenji, YAMAKAWA Tetsu  触媒 = Catalysts & Catalysis  49-  (6)  409  -411  2007/09/05
• Chemistry of Chelate-Type Hypervalent Born and Aluminum : Utilization for Selective Organic Synthesis

  URAGUCHI Daisuke, OOI Takashi, MARUOKA Keiji  J. Synth. Org. Chem. Jpn.  58-  (1)  14-22  -22  2000/01  [Refereed][Invited]
   

  In this review, the hypercoordination of boron and aluminum as typical main group elements is embodied, and their synthetic utility is demonstrated with several synthetic examples. B and Al Lewis acids are found to be successfully utilized in several chelation-controlled reactions of various substrates (alkoxy carbonyl compounds, fluoro carbonyl compounds, fluoro epoxides, and alkoxy epoxides) via unprecedented pentacoordinate chelate-type complex formation by taking advantage of the exceedingly high affinity of B and Al to fluorine and oxygen, and hence, contrary to the previous observations, can be classified as chelating Lewis acid reagents rather than non-chelating Lewis acids. In addition to the experimental demonstration, such pentacoordinate complex formation of B and Al Lewis acids with various bidentate substrates is also characterized by low-temperature ¹H, ¹³c, ¹¹B, ²⁷AlNMR spectroscopy.

Books etc

• 有機光反応の化学 : 光が誘起する電子移動・触媒系・有機合成

  浦口 大輔, 大井 貴史 (Contributor光電子移動条件下での有機イオン対触媒による立体制御)
  化学同人 2022/03 (ISBN: 9784759814033) v, 209p, 図版 [4] p
• Supramolecular Catalysis: New Directions and Developments

  Kohsuke Ohmatsu, Daisuke Uraguchi, Takashi Ooi (P.W.N.M.van Leeuwen, Matthieu Rayna) (ContributorAssembled Ionic Molecular Catalysts and Ligands)
  Wiley-VCH 2022/01 (ISBN: 9783527349029)
• Molecular Technology: Synthesis Innovation, Volume 4, H. Yamamoto and T. Kato Eds.

  Daisuke Uraguchi, Kohsuke Ohmatsu, Takashi Ooi (Joint work)
  Wiley-VCH 2019 163-197
• 「多機能型キラルオニウム塩の設計に基づく高選択的分子変換」“有機分子触媒の開発と工業利用”

  大松 亨介, 浦口 大輔, 大井 貴史 (Joint work第4章)
  シーエムシー出版 2018/03 Chap 4
• CSJカレントレビュー「有機分子触媒の化学」

  浦口 大輔, 大井 貴史 (Joint work「イオン対を中心とした不斉塩基触媒」)
  化学同人 2016/11 (ISBN: 9784759813821) 244 -
• Site-Selective Conjugate Addition Through Catalytic Generation of Ion- Pairing Intermediates (in Site Selective Catalysis (Topics in Current Chemistry))

  Daisuke Uraguchi, Takashi Ooi (Joint work)
  Springer 2016/03 (ISBN: 3319263315) -
• Comprehensive Enantioselective Organocatalysis

  Uraguchi, Daisuke, Kohsuke, Ohmatsu, Ooi, Takashi (Joint work)
  Wiley-VCH Verlag GmbH 2013 in press
• Comprehensive Chirality

  Daisuke Uraguchi, Takashi Ooi (Joint work)
  Elsevier Science 2012 00
• Stereoselective Synthesis of Drugs and Natural Products

  Kohsuke Ohmatsu, Daisuke Uraguchi, Takashi Ooi (Joint work)
  John Wiley & Sons Inc. 2012 00
• (3R,5R,8R)- 3,8-Bis(1-methylethyl)-2,2,7, 7-tetrakis(4-methylphenyl)-1,4,6,9- tetraaza-5λ5-phosphaspiro[4,4]non- 5-ene, Hydrochloride salt (1:1)

  Daisuke Uraguchi, Takashi Ooi (Joint work)
  Wiley-VCH 2012 RN01546

Presentations

• キラル有機イオン対の触媒化学  [Invited]

  浦口 大輔

  2021年度有機合成化学協会九州山口支部講演会「合成有機化学のフロンティア」  2021/06
• 非求核的キラルアニオンの触媒化学： O,N,N,O型四座配位子をもつキラルボラートの創製と機能評価  [Invited]

  浦口 大輔

  統合物質創製化学研究推進機構 第6回国内シンポジウム「物質創製化学の精密戦略」  2021/01
• 非求核的キラルアニオンの触媒化学： O,N,N,O型四座配位子をもつキラルボラートの創製と機能評価  [Invited]

  浦口 大輔

  第13回有機触媒シンポジウム  2020/12
• 有機イオン対の触媒化学

  浦口 大輔

  第434回触媒科学研究所コロキウム  2020/12
• 形をもった「塩」は分子を操ることができるか  [Invited]

  浦口 大輔

  第6回名古屋大学の卓越・先端・次世代研究シンポジウム  2020/01
• カチオンの制御を担う非求核的キラルアニオンの創製  [Invited]

  浦口 大輔

  生産技術・商品開発ディビジョン講演会  2019/11
• 有機イオン対の触媒化学  [Invited]

  浦口 大輔

  第一回 Central Science Symposium  2019/09
• 魔女の雑草をだます薬  [Invited]

  浦口 大輔

  先端化学研究部 有機合成化学ミニシンポジウム  2019/09
• 有機イオン対の触媒化学  [Invited]

  浦口 大輔

  先端化学研究部 有機合成化学ミニシンポジウム  2019/09
• 魔女の雑草をだます薬

  浦口 大輔

  第4回先端ケミカルバイオロジー研究会  2019/06
• 魔女の雑草をだます薬ーセレンディピティが導いた融合研究  [Invited]

  浦口大輔

  第22回農薬相模セミナー  2019/01  公財）相模中央化学研究所大会議室  公財）相模中央化学研究所
  
• P－スピロ型キラルアミノホスホニウム骨格が拓く触媒化学  [Invited]

  浦口大輔

  第45回有機典型元素化学討論会  2018/12  朱鷺メッセ新潟コンベンションセンター
• キラル有機カチオン触媒による多重選択性の同時制御  [Invited]

  浦口大輔

  第13回プロセス化学ラウンジ  2018/11  富士フイルム和光純薬株式会社 湯河原研修所
• 有機イオンペアが織りなす反応場を使った有機合成  [Invited]

  浦口大輔

  CSJフェスタ2018 フェスタ企画 テーマ企画：これぞ日本が誇る有機合成化学！～多彩な反応から暮らしに役立つ製品開発まで～  2018/10  タワーホール船堀
• Molecular Design, Synthesis, and Asymmetric Catalysis of a Hexacoordinated Chiral Phosphate Ion  [Invited]

  Uraguchi Daisuke

  International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)  2018/08  Kyoto Univ.
• 多官能性分子の合成戦略：P－スピロ型アミノホスホニウムイオンによる多重選択性制御  [Invited]

  浦口 大輔

  第３５回メディシナルケミストリーシンポジウム（MCS2017）  2017/10  名古屋大学  日本薬学会
  
• キラル有機イオン対の触媒化学  [Invited]

  浦口 大輔

  第2回分子性触媒若手セミナー  2017/10  東京農工大学
• Betaine-Type Electron-Transfer Catalyst: Design and Application  [Invited]

  Daisuke Uraguchi

  International Symposium on Pure & Applied Chemistry (ISPAC) 2017  2017/06  Hotel Continental Saigon  International Symposium on Pure & Applied Chemistry (ISPAC) 2017
  
• デザイン型有機イオン対の触媒化学  [Invited]

  浦口大輔

  有機合成2月セミナー 有機合成のニュートレンド2017  2017/02  大阪科学技術センター  有機合成化学協会関西支部
  
• Highly Stereoselective Transformations under the Catalysis of P-Spiro Chiral Tetraaminophosphonium Salts  [Invited]

  Daisuke Uraguchi

  21st International Conference on Organic Synthesis (ICOS21)  2016/12  Indian Institute of Technology, Bombay (IIT, Bombay)  21st International Conference on Organic Synthesis (ICOS21)
  
• デザイン型有機イオンの力を活かした触媒化学  [Invited]

  浦口大輔

  CSJフェスタ2016 コラボレーション企画 文科省科研費 新学術領域研究「有機分子触媒」特別企画：有機分子触媒による未来型分子変換  2016/11  タワーホール船堀  新学術領域研究「有機分子触媒」総括班
  
• キラルアミノホスホニウム塩を用いる触媒的分子変換  [Invited]

  浦口大輔

  分子研研究会 「若い世代が創る次世代型分子触媒の開発とその展望」  2016/11  分子化学研究所  分子化学研究所
  
• キラルアミノホスホニウム塩／可視光増感剤の協働触媒作用による不斉ラジカル反応  [Invited]

  浦口 大輔

  JST ACT-C 不斉 炭素-炭素結合形成反応・若手ワークショップ  2016/03  ホテルグランドヒ市ヶ谷
• キラルアミノホスホニウム塩の構造制御を基盤とした高選択的分子変換  [Invited]

  浦口 大輔

  Organic Seminar「有機合成化学の可能性：反応性と選択性をいかに制御するか」  2016/01  ベンチャーホール・名古屋大学
• Asymmetric catalysis of P-spiro chiral tetraaminophosphonium salts  [Invited]

  Daisuke Uraguchi

  Pacifichem 2015 "Recent Trends in Organocatalysis"  2015/12  Hilton Hawaiian Village
• キラル有機イオン対の触媒化学  [Invited]

  浦口大輔

  公益財団法人相模中央化学研究所「創立５０周年記念講演会」  2015/10  一橋講堂  公益財団法人相模中央化学研究所
  
• Catalysis of Chiral Aminophosphonium Salts  [Not invited]

  Daisuke Uraguchi

  Lectureship Award MBLA 10th Anniversary Special Lectures  2015/03  日本大学（船橋キャンパス）  Banyu Life Science Foundation International
  
• キラルアミノホスホニウム塩の構造制御に基づく高選択的分子変換法の開拓  [Not invited]

  浦口大輔

  第45回中部化学関係学協会支部連合秋季大会 特別討論会「創発する有機化学」  2014/11  中部大学（春日井キャンパス）
• Catalysis of P-Spiro Chiral Aminophosphonium Salts  [Not invited]

  Daisuke Uraguchi

  Advanced Molecular Transformations by Organocatalysts 2nd International Conference & 7th Symposium on Organocatalysis  2014/11  東京大学  新学術領域「有機分子触媒による未来型分子変換」総括班
  
• P－スピロ型アミノホスホニウム塩を用いる触媒的分子変換  [Not invited]

  浦口大輔

  理研シンポジウム: 第9回有機合成化学のフロンティア  2014/06  理化学研究所 和光研究所 鈴木梅太郎ホール
• 水素結合供与型アミノホスホニウム塩を用いる触媒的不斉合成  [Not invited]

  浦口大輔

  「有機分子触媒による未来型分子変換」第4回公開シンポジウム(分子活性化－有機分子触媒合同シンポジウム)  2014/06  北海道大学学術交流会館  新学術領域「有機分子触媒による未来型分子変換」総括班
  
• キラル有機イオン対触媒の創製と機能創出  [Not invited]

  浦口大輔

  第24回 万有福岡シンポジウム グリーンサスティナブルケミストリーを指向した有機合成－有機合成が世界を救う  2014/06  九州大学医学部百年講堂  万有福岡シンポジウム実行委員会
  
• Catalysis of Chiral Aminophosphonium Salts  [Not invited]

  Daisuke Uraguchi

  Lectureship Award MBLA 10th Anniversary Special Lectures  2014/03  日本大学（船橋キャンパス）
• アミノホスホニウム塩の構造制御に基づく触媒機能の創出  [Not invited]

  浦口 大輔

  合同シンポジウム- 日本プロセス化学会 2013 ウインターシンポジウム・新学術領域研究「有機分子触媒による未来型分子変換」第3回公開シンポジウム-  2013/11  仙台市民会館  新学術領域「有機分子触媒による未来型分子変換」総括班
  
• キラルイミノホスホランを有機塩基触媒とする高選択的分子変換  [Not invited]

  浦口大輔

  薬学会年会シンポジウム「有機合成化学の若い力」  2013/03  パシフィコ横浜  日本薬学会
  
• キラルアミノホスホニウム塩を触媒とする高選択的分子変換  [Not invited]

  浦口大輔

  日本化学会春季年会「有機分子触媒の最先端」  2013/03  立命館大学草津キャンパス
• Chiral Ionic Brønsted Acid-Achiral Brønsted Base Synergistic Catalysis for Asymmetric Sulfa-Michael Addition to Nitroolefins  [Not invited]

  Daisuke Uraguchi

  First Japan -USA Organocatalytic Symposium  2012/12  Waikiki Prince Hotel, Hawaii
• P－スピロ型キラルアミノホスホニウム塩の触媒作用  [Not invited]

  浦口大輔

  新学術領域研究「有機分子触媒による未来型分子変換」第1回全体会議  2012/06  京都大学  新学術領域研究「有機分子触媒による未来型分子変換」総括班
  
• アニオン認識型キラルオニウム塩の創製と触媒的不斉合成への応用  [Not invited]

  浦口大輔

  日本化学会第92春季年会  2012/03  慶應義塾大学
• 多機能型キラルオニウム塩の設計に基づく高選択的分子変換法の開拓  [Not invited]

  浦口大輔

  新学術領域研究「有機分子触媒による未来型分子変換」第1回公開シンポジウム  2012/01  新学術領域研究「有機分子触媒による未来型分子変換」総括班
  

Association Memberships

• Synthetic Organic Chemistry Japan   ACS   CSJ   

Research Projects

• Development of cationic main-group catalyst for direct control of radical species

  Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)

  Date (from‐to) : 2022/04 -2025/03 

  Author : 浦口 大輔
• 高反応性カチオン種の制御を志向した非配位性キラルアニオンの化学

  日本学術振興会：科学研究費助成事業

  Date (from‐to) : 2019/04 -2022/03
• Development of Cooperative Catalysis of Chiral Ion Pair

  Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research

  Date (from‐to) : 2016/04 -2019/03 

  Author : Uraguchi Daisuke

   

  A series of chiral ion pair catalysts has been developed for precise regulation of C-C bond formations requiring (multiple) selectivity control. For example, by use of our iminophosphorane catalysts, virtually complete control of regio-, diastereo-, and enantioselectivities was realized in the extended conjugate addition and its diastereoselectivity was successfully reversed through very small modification of the catalyst structure. Development of a chiral non-cordinating anion consisting from phosphorus and tridentate chiral ligands is another remarkable achievement of the program. Furthermore, an intramolecular ion pair having a single-electron transfer ability debuted to the organic molecular catalysis arena during the program period.
• Chemical genetic approach toward eradication of noxious parasitic weed Striga hermonthica

  Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research

  Date (from‐to) : 2015/07 -2018/03 

  Author : Tsuchiya Yuichiro, URAGUCHI Daisuke, KUWATA Keiko, SATO Ayato

   

  A nixious parasitic plant called Striga hermonthica (Striga) represents a major threat to food security in Africa. In this research project, I focused on a host-depent germination mechanism in Striga and use it to develop a specific herbicide that lead the seeds to "suicide germination". The developed molecule (code name : SAMR690), which is composed of synthetic scaffold connected with the active core structure of strigolactones, exhibits extraordinary potency in stimulating Striga germination at femto-molar range without impinging on beneficial functions in the host strigolactone-related processes. Most importantly, the three-step procedure for synthesizing SAMO-Me-690 greatly increases the potential for Striga eradication via suicide germination campaigns in Africa.
• A Novel Catalysis of Photoexcited Ketones

  Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research

  Date (from‐to) : 2016/04 -2017/03 

  Author : Uraguchi Daisuke

   

  Study on the development of a new catalytic function of photoexcited ketones was pursued. The high catalytic activity of the ketones was confirmed in a model reaction which was designed for evaluating the expected new catalytic function. However, the mechanistic analysis by the physicochemical approach is not completed yet and I could not come to clarify the details the catalysis within a study period. On the other hand, I conducted some experimental analyses on photoexcited imines which have been regarded as a ketone analog in synthetic chemistry. Markedly, new photophysical properties were found in this study and these finding will open the door to a new field of the photochemistry.
• 有機分子触媒による未来型分子変換「多機能型キラルオニウム塩の設計に基づく高選択的分子変換法の開拓」

  科学研究費助成事業

  Date (from‐to) : 2011/07 -2016/03 

  Author : 浦口大輔
• キラル有機イオン対の構造制御を基盤とした触媒的分子変換プロセスの開発

  日本学術振興会：科学研究費助成事業

  Date (from‐to) : 2011/11 -2015/03
• 水素結合供与型テトラアミノホスホニウム－過オキソ酸の創製と精密合成反応への応用

  日本学術振興会：科学研究費助成事業

  Date (from‐to) : 2011/04 -2013/03
• 新規カチオン型光学活性ブレンステッド酸触媒の創製と応用

  日本学術振興会：科学研究費助成事業

  Date (from‐to) : 2009/04 -2011/03 

  Author : 浦口大輔
• Molecular Design and Synthetic Applications of Chiral Aminophosphonium Salts

  Japan Society for the Promotion of Science：Grants-in-Aid for Scientific Research

  Date (from‐to) : 2008 -2010 

  Author : OOI Takashi, URAGUCHI Daisuke, OHMATSU Kohsuke

   

  A series of P-spiro chiral tetraaminophosphonium salts have been designed and synthesized as a new class of organic molecular catalysts, and their inherent abilities to exert four different, synthetically relevant asymmetric catalyses have been brought out through the unique molecular design on a single core structure, N_4P^+. Further, these catalyses have been applied to the development of various C-C, C-P, and C-N bond-forming reactions, in which the remarkably high catalytic performances and stereocontrolling abilities of the chiral tetraaminophosphonium salts have been successfully demonstrated.
• 水素結合型トリアミノイミノホスホラン骨格を有する不斉有機強塩基触媒の創製

  科学研究費助成事業

  Date (from‐to) : 2007/04 -2009/03 

  Author : 浦口 大輔
• 水素結合受容型有機リン触媒の創製と不斉合成反応への利用

  文部科学省：科学研究費助成事業

  Date (from‐to) : 2006/04 -2007/03 

  Author : 浦口 大輔
• 典型金属イオンをルイス酸触媒とする完全水中反応の実現と次世代型不斉合成への展開

  日本学術振興会：科学研究費助成事業

  Date (from‐to) : 2002 -2004 

  Author : 浦口 大輔

   

  本年度は、他の高エナンチオ選択的合成反応の開発を目指し、リン酸配位子の構造修飾と、金属陽イオンの最適化を行った。モデル反応としてマンニッヒ反応を用い、これまで有機溶媒中での利用が困難であった基質を視野に入れた反応系の構築を計画して研究に着手したが、現在までのところ従来汎用されるイミンを用いるに留まっている。具体的なリン酸配位子としては、構造修飾の可能性が広いリン酸ジエステルとして、ビナフトール誘導体に代表されるような光学活性ジオールを有するリン酸エステルを種々導入した配位子を合成した。NMRによる複合体形成の確認実験では、これらの配位子は効果的にイミン化合物と錯形成を行うことを明らかにすることができた。実際にこれらの配位子を用いたマンニッヒ反応を、種々の金属イオン前駆体及び金属イオンフリーの条件下で反応を行った結果、驚くべきことに金属イオンの添加なしに反応は速やかに進行し、高い選択性を与えることがわかった。本反応は新規ブレンステッド酸触媒を用いる金属非存在下における高選択的炭素-炭素結合形成反応であり、合成化学的に非常に有用な反応系の創出に繋がると期待される。ブレンステッド酸触媒を用いる不斉合成反応の実現は従来非常に困難と考えられてきたが、本リン酸配位子の利用によりこれまで長年の懸案であった問題点を解決する新たなアプローチ法を提供した。

Industrial Property Rights

• JP 2017014149 A 20170119:Striga germination regulating agent and a stria germination control method using the same  2016年/07/01

  Tsuchiya, Yuichiro, Uraguchi, Daisuke, Sathiyanarayanan, A. M, Kinoshita, Toshinori, Oi, Takashi  Nagoya University
• WO 2017002898 A1 20170105:Striga germination regulating agent and a stria germination control method using the same  2016年/06/30

  Tsuchiya, Yuichiro, Uraguchi, Daisuke, Sathiyanarayanan, Arumugam Murugan, Hagihara, Shinya, Yoshimura, Masahiko, Kinoshita, Toshinori, Ooi, Takashi, Itami, Kenichiro  Nagoya University
• 5757022:Optically active β-aminoalcohols and their use for preparation of optically active alkylaminosulfonamides    2015/06/12

  Ooi, Takashi, Uraguchi, Daisuke  Nagoya University
• 5527923:Preparation of perfluoroalkylated heterocyclic compounds    2014/04/25

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5478095:Method for the preparation of arylpyridines    2014/02/21

  Yamakawa, Tetsu, Kobayashi, Osamu, Uraguchi, Daisuke  (財)相模中央化学研究所，東ソー(株)
• 5458303:Preparation of optically active arylaminophosphonium salt as catalyst for the asymmetric synthesis, and method for preparation of optically active β-aminonitroalkanes    2014/01/24

  Ooi, Takashi, Uraguchi, Daisuke  三井化学(株)，名古屋大学
• 5424283:PRODUCTION METHOD OF α,β-UNSATURATED CARBONYL COMPOUND HAVING PERFLUOROALKYL GROUP    2013/12/06

  Yamakawa, Tetsu, Yamamoto, Kyoko, Otsuka, Yuki, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5396578:Chiral tetraaminophosphonium salts, catalyst for asymmetric synthesis and method for producing chiral β-nitroalcohol    2013/11/01

  Ooi, Takashi, Uraguchi, Daisuke  三井化学(株)，名古屋大学
• 5266485:Preparation of optically active tetraaminophosphonium salts, catalysts for the asymmetric synthesis reactions, asymmetric synthesis reaction, and asymmetric-synthesis method of tetrasubstituted α-amino-acid containing peptide    2013/05/17

  Ooi, Takashi, Uraguchi, Daisuke  三井化学(株)，名古屋大学
• 5238172:Perfluoroalkyl nitrogen-containing 6-membered ring compound and process for the preparation thereof    2013/04/05

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5203144:Preparation of styrenes from vinylmagnesium halides and chlorobenzenes    2013/02/22

  Yamakawa, Tetsu, Yamamoto, Tetsuya, Uraguchi, Daisuke  (財)相模中央化学研究所，東ソー(株)
• 5198780:Preparation of (fluoro)hydroxyalkamide compounds    2013/02/15

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5189345:REACTION REAGENT FOR TRIFLUOROMETHYLATION    2013/02/01

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5173335:The manufacturing method of (1-perfluoroalkyl) vinyl aryl    2013/01/11

  Yamakawa, Tetsu, Kobayashi, Osamu, Uraguchi, Daisuke  (財)相模中央化学研究所，東ソー・エフテック(株)
• 5106048:One-pot preparation of (perfluoroalkyl)benzenes    2012/10/12

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5093798:Process for the preparation of α,β-unsaturated carbonyl compound containing perfluoroalkyl group    2012/09/28

  Yamakawa, Tetsu, Yamamoto, Kyoko, Otsuka, Yuki, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5090711:Preparation of 2,6-diamino-8,8-bis(perfluoroalkyl)-8H-purines    2012/09/21

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5067780:Preparation of (perfluoroalkyl)quinolines    2012/08/24

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• 5053622:NUCLEIC ACID BASES HAVING PERFLUOROALKYL GROUP AND METHOD FOR PRODUCING THE SAME    2012/08/03

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• JP-A- JP-2011190181:Method for the preparation of optically active compound using chiral ammonium betaine  2011年/09/29

  Ooi, Takashi, Uraguchi, Daisuke  Nagoya University
• US-A1-2009131716:Chiral tetraaminophosphonium salts, catalyst for asymmetric synthesis and method for producing chiral β-nitroalcohol  2009年/05/21

  Ooi, Takashi, Uraguchi, Daisuke  三井化学(株)，名古屋大学
• WO-A1-2007055170-2007-05-18:Process for the preparation of nucleic acid base having perfluoroalkyl group  2006年/05/18

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)，東ソー(株)
• WO-A1-2007056667-2008-05-15:Reaction reagent for trifluoromethylation of benzene and heterocyclic ring  2006年/05/15

  Yamakawa, Tetsu, Yamamoto, Kyoko, Uraguchi, Daisuke, Tokuhisa, Kenji  (財)相模中央化学研究所，東ソー・エフテック(株)
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