研究者詳細 - 大井　貴史

論文 - 大井　貴史

分割表示 203 件中 81 - 100 件目／全件表示 >>

Enantioselective Protonation of α-Hetero Carboxylic Acid-Derived Ketene Disilyl Acetals under Chiral Ionic Brønsted Acid Catalysis 査読有り

Daisuke Uraguchi, Tomohito Kizu, Yuki Ohira, Takashi Ooi

Chem. Commun. 2014 巻 ( 50 ) 頁： 13489-13491 2014年

Chiral Ammonium Betaine-Catalyzed Highly Stereoselective Aza-Henry Reaction of α-Aryl Nitromethanes with Aromatic N-Boc Imines 査読有り

Daisuke Uraguchi, Keigo Oyaizu, Haruhiro Noguchi, Takashi Ooi

Chem. Asian J. 2014 巻 ( 10 ) 頁： 334-337 2014年

Highly Stereoselective Michael Addition of Azlactones to Electron-Deficient Triple Bonds under P-Spiro Chiral Iminophosphorane Catalysis: Importance of Protonation Pathway 査読有り

Uraguchi, Daisuke; Ueki, Yusuke; Sugiyama, Atsushi; Ooi, Takashi

Chem. Sci. 4 巻頁： in press 2013年1月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

A catalyst-controlled, geometrically divergent asymmetric Michael addition of azlactones to methyl propiolate has been achieved under the catalysis of P-spiro chiral triaminoiminophosphoranes. An uncommon O-protonation of the intermediary allenic enolate is proposed to rationalize geometric control and its validity is proven by the development of highly Z- and enantioselective Michael addition of azlactones to cyanoacetylene with broad substrate scope.

DOI： 10.1039/C2SC22027J

Carbene Transfer from Triazolylidene Gold Complexes as a Potent Strategy for Inducing High Catalytic Activity 査読有り

Daniel Canseco-Gonzalez, Ana Petronilho, Helge Mueller-Bunz, Kohsuke Ohmatsu, Takashi Ooi, Martin Albrecht

J. Am. Chem. Soc. 135 巻 ( 35 ) 頁： 13193-13203 2013年

Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3-Substituted Oxindoles 査読有り

Kohsuke Ohmatsu, Yuichiro Ando, Takashi Ooi

J. Am. Chem. Soc. 135 巻 ( 50 ) 頁： 18706-18709 2013年

Catalytic Asymmetric Oxidation of N-Sulfonyl Imines with Hydrogen Peroxide－Trichloroacetonitrile System 査読有り

Daisuke Uraguchi, Ryosuke Tsutsumi, and Takashi Ooi

J. Am. Chem. Soc. 2013 巻 ( 135 ) 頁： 8161-8164 2013年

Exploiting the Modularity of Ion-Paired Chiral Ligands for Palladium-Catalyzed Enantioselective Allylation of Benzofuran-2(3H)-ones 査読有り

Kohsuke Ohmatsu, Mitsunori Ito, Tomoatsu Kunieda, and Takashi Ooi

J. Am. Chem. Soc. 135 巻 ( 2 ) 頁： 590–593 2012年12月

Highly Regio-, Diastereo-, and Enantioselective 1,6- and 1,8-Additions of Azlactones to Di- and Trienyl N-Acylpyrroles 査読有り

Uraguchi, Daisuke; Yoshioka, Ken; Ueki, Yusuke; Ooi, Takashi

J. Am. Chem. Soc. 134 巻 ( 47 ) 頁： 19370–19373 2012年11月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

A vinylog of Michael addition (1,6-addition) of azlactones to δ-substituted dienyl N-acylpyrroles has been developed with virtually complete 1,6-, diastereo-, and enantioselectivities by means of chiral P-spiro triaminoiminophosphorane as a catalyst. This system has been successfully extended to an unprecedented bis-vinylog of Michael addition (1,8-addition) of azlactones to ζ-substituted trienyl N-acylpyrroles with high levels of regio- and stereocontrol.

DOI： 10.1021/ja310209g

Chiral Ionic Brønsted Acid-Achiral Brønsted Base Synergistic Catalysis for Asymmetric Sulfa-Michael Addition to Nitroolefins 査読有り

Uraguchi, Daisuke; Kinoshita, Natsuko; Nakashima, Daisuke; Ooi, Takashi

Chem. Sci. 3 巻 ( 11 ) 頁： 3161-3164 2012年7月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

A highly enantioselective sulfa-Michael addition to aromatic and aliphatic nitroolefins is achieved under the synergistic catalysis of chiral, ionic Brønsted acid homo-1b·HBArF and 2,6-lutidine. The potential utility of this new method is clearly demonstrated by its application to the syntheses of a novel, optically active taurine derivative and β-sultam.

DOI： 10.1039/C2SC20698F

Nitroolefins as a Nucleophilic Component for Highly Stereoselective Aza-Henry Reaction under the Catalysis of Chiral Ammonium Betaines 査読有り

Uraguchi, Daisuke; Oyaizu, Keigo; Ooi, Takashi

Chem. Eur. J. 18 巻 ( 27 ) 頁： 8306–8309 2012年7月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Vinylogous nitronate was successfully generated from β,β-disubstituted nitroolefins for achieving a highly regio-, diastereo-, and enantioselective aza Henry reaction under the influence of chiral ammonium betaine of type 1 as an organic-base catalyst. The present approach greatly expands the synthetic utility of nitroolefins in the development of carbon-carbon bond-forming reactions.

DOI： 10.1002/chem.201201259

Catalytic Asymmetric Mannich-Type Reactions of α-Cyano α-Sulfonyl Carbanions 招待有り査読有り

Ohmatsu, Kohsuke; Goto, Ayano; Ooi, Takashi

Chem. Commun. 48 巻 ( 64 ) 頁： 7913-7915 2012年5月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

An efficient asymmetric Mannich-type reaction of α-cyano α-sulfonyl carbanions has been achieved by exploiting the structural modularity and anion-recognition ability of chiral 1,2,3-triazolium ions. This protocol has proven to be applicable to a variety of N-Boc imines and cyanosulfones, affording β-amino α-cyanosulfones in excellent yields with high stereoselectivities.

DOI： 10.1039/C2CC32398B

Catalytic Asymmetric Ring Openings of Meso and Terminal Aziridines with Halides Mediated by Chiral 1,2,3-Triazolium Silicates 査読有り

Ohmatsu, Kohsuke; Hamajima, Yuta; Ooi, Takashi

J. Am. Chem. Soc. 134 巻 ( 21 ) 頁： 8794–8797 2012年5月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Catalytic asymmetric chloride and bromide ring openings of meso aziridines with trimethylsilyl halides have been developed using modular chiral 1,2,3-triazolium chlorides as catalysts. Control experiments suggest the reaction pathway involving hypervalent silicate ions as reactive intermediates. The application of this system to the efficient kinetic resolution of terminal aziridines is also reported.

DOI： 10.1021/ja3028668

Ionic Nucleophilic Catalysis of Chiral Ammonium Betaines for Highly Stereoselective Aldol Reaction from Oxindole-Derived Vinylic Carbonates 査読有り

Uraguchi, Daisuke; Koshimoto, Kyohei; Ooi, Takashi

J. Am. Chem. Soc. 134 巻 ( 16 ) 頁： 6972–6975 2012年4月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

A new strategy for developing stereoselective bond-forming reactions is introduced; it takes advantage of the ionic nucleophilic catalysis of chiral ammonium betaines to utilize vinylic esters simultaneously as the enolate precursor and the acylating agent for coupling with electrophiles. Its synthetic utility is clearly demonstrated by the realization of a highly diastereo- and enantioselective aldol reaction from oxindole-derived vinylic carbonates.

DOI： 10.1021/ja3022939

Base-Catalyzed Direct Aldolization of α-Alkyl-α-Hydroxy Trialkyl Phosphonoacetates 査読有り

Corbett, Michael; Uraguchi, Daisuke; Ooi, Takashi; Johnson, Jeffrey

Angew. Chem. Int. Ed. 51 巻 ( 19 ) 頁： 4685–4689 2012年4月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Pass the P: Catalytic direct aldol addition of α-hydroxy trialkyl phosphonacetates to aldehydes affords α-hydroxy-β-phosphonyloxy ester products. The fully substituted glycolate enolate intermediate is generated in situ under mild conditions by a [1,2] phosphonate-phosphate rearrangement. High enantioselectivity and dramatic enhancement of reaction diastereocontrol is realized by the application of chiral iminophosphorane catalysts.

DOI： 10.1002/anie.201200559

Ion-paired chiral ligands for asymmetric palladium catalysis 査読有り

Ohmatsu, Kohsuke; Ito, Mitsunori; Kunieda, Tomoatsu; Ooi, Takashi

Nature Chemistry 4 巻頁： 473–477 2012年4月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Conventional chiral ligands rely on the use of a covalently constructed, single chiral molecule embedded with coordinative functional groups. Here, we report a new strategy for the design of a chiral ligand for asymmetric transition-metal catalysis; our approach is based on the development of an achiral cationic ammonium-phosphine hybrid ligand paired with a chiral binaphtholate anion. This ion-paired chiral ligand imparts a remarkable stereocontrolling ability to its palladium complex, which catalyses a highly enantioselective allylic alkylation of α-nitrocarboxylates. By exploiting the possible combinations of the achiral onium entities with suitable coordinative functionalities and readily available chiral acids, this approach should contribute to the development of a broad range of metal-catalysed, stereoselective chemical transformations.

DOI： 10.1038/nchem.1311

Highly Stereoselective Catalytic Conjugate Addition of Acyl Anion Equivalent to Nitroolefins 査読有り

Uraguchi, Daisuke; Ueki, Yusuke; Ooi, Takashi

Chem. Sci. 3 巻 ( 3 ) 頁： 842-845 2011年11月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Highly enantioselective conjugate addition of 2-unsubstituted azlactone 3 to various nitroolefins 4 was accomplished by the selective utilization of supramolecularly assembled, chiral tetraaminophosphonium aryloxide-arylhydroxide 1a·[2a]2 as a requisite catalyst. The key to this achievement is the polarity dependence of the molecular associations of type 1·[2]n and the crucial role of the proximal arylhydroxide 2 as a proton donor. The present method offers an attractive route to various optically active amino carbonyl compounds including β2-amino acids.

DOI： 10.1039/C1SC00678A

Enantioselective Aza-Michael Addition to Conjugated Nitroenynes Catalyzed by Chiral Arylaminophosphonium Barfates 招待有り査読有り

Uraguchi, Daisuke; Kinoshita, Natsuko; Kizu, Tomohito; Ooi, Takashi

Synlett ( 9 ) 頁： 1265-1267 2011年4月

担当区分：筆頭著者記述言語：英語掲載種別：研究論文（学術雑誌）

Enantioselective aza-Michael addition to conjugated nitroenynes has been developed. P-Spiro heterochiral arylaminophosphonium barfate 1bBArF effectively catalyzes the reaction, and the corresponding conjugate adducts, β-amino homopropargylic nitro compounds, are obtained in good chemical yields with high enantioselectivities.

DOI： 10.1055/s-0030-1260541

Chiral 1,2,3-Triazoliums as New Cationic Organic Catalysts with Anion-Recognition Ability: Application to Asymmetric Alkylation of Oxindoles 査読有り

Ohmatsu, Kohsuke, Kiyokawa, Mari, Ooi, Takashi

J. Am. Chem. Soc. ( 133 ) 頁： 1307–1309 2011年

Controlled Assembly of Chiral Tetraaminophosphonium Aryloxide Arylhydroxide(s) in Solution 査読有り

Uraguchi, Daisuke; Ueki, Yusuke; Ooi, Takashi

Angew. Chem. Int. Ed. ( 50 ) 頁： 3681–3683 2011年

Precise Control of Spontaneous Molecular Assembly of Chiral Tetraaminophosphonium Aryloxide-Arylhydroxide(s) in Solution 査読有り

Uraguchi, Daisuke; Ueki, Yusuke; Ooi, Takashi

Angew. Chem. Int. Ed. 2011 巻 ( 50 ) 頁： 3681-3683 2011年

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