Kinetic Resolution of Racemic α-Arylalkanoic Acids with Achiral Alcohols via the Asymmetric Esterification Using Carboxylic Anhydrides and Acyl-Transfer Catalysts

被引：113

作者：

Shiina, Isamu ^{[1
]}

Nakata, Kenya ^{[1
]}

Ono, Keisuke ^{[1
]}

Onda, Yu-suke ^{[1
]}

Itagak, Makoto ^{[2
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

[2] Sumitomo Chem Co Ltd, Organ Synth Res Lab, Konohana Ku, Osaka 5548558, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 33期

关键词：

ENANTIOSELECTIVE ADDITION; TETRAMISOLE DERIVATIVES; BENZOIC ANHYDRIDES; KETENES; BENZOTETRAMISOLE; LACTONES; ESTERS; ARYL;

D O I：

10.1021/ja103490h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A variety of optically active carboxylic esters are produced by the kinetic resolution of racemic alpha-substituted carboxylic acids using achiral alcohols, aromatic or aliphatic carboxylic anhydrides, and chiral acyl-transfer catalysts. The combination of 4-methoxybenzoic anhydride (PMBA) or pivalic anhydride with the modified benzotetramisole-type catalyst ((S)-beta-Np-BTM) is the most effective for promotion of the enantioselective coupling reaction between racemic carboxylic acids and a novel nucleophile, bis(alpha-naphthyl)methanol, to give the corresponding esters with high ee's. This protocol was successfully applied to the production of nonracemic nonsteroidal anti-inflammatory drugs from racemic compounds utilizing the transacylation process to generate the mixed anhydrides from the acid components with the suitable carboxylic anhydrides.

引用

页码：11629 / 11641

页数：13

共 39 条

[21] Kinetic resolution of α-acetoxy N-acyl oxazolidinethiones by a chiral O-nucleophilic acyl transfer catalyst [J].

Notte, GT ;

Sammakia, T ;

Steel, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) :13502-13503

[22] METHODS FOR THE SYNTHESIS OF ANTIINFLAMMATORY 2-ARYL PROPIONIC ACIDS [J].

RIEU, JP ;

BOUCHERLE, A ;

COUSSE, H ;

MOUZIN, G .

TETRAHEDRON, 1986, 42 (15) :4095-4131

[23] 3-Pyrroline-1-carbonyl (Pyroc) Group: A Removable Protecting Group for the Kinetic Resolution of Racemic Carboxylic Acids and Alcohols through Catalytic Asymmetric Acylation [J].

Sakakura, Akira ;

Umemura, Shuhei ;

Ishihara, Kazuaki .

SYNLETT, 2009, (10) :1647-1650

[24] Catalytic asymmetric couplings of ketenes with aldehydes to generate enol esters [J].

Schaefer, C ;

Fu, GC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (29) :4606-4608

[25] An effective use of benzoic anhydride and its derivatives for the synthesis of carboxylic esters and lactones: A powerful and convenient mixed anhydride method promoted by basic catalysts [J].

Shiina, I ;

Kubota, M ;

Oshiumi, H ;

Hashizume, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :1822-1830

[26] The first asymmetric esterification of free carboxylic acids with racemic alcohols using benzoic anhydrides and tetramisole derivatives: an application to the kinetic resolution of secondary benzylic alcohols [J].

Shiina, Isamu ;

Nakata, Kenya .

TETRAHEDRON LETTERS, 2007, 48 (47) :8314-8317

[27] Total synthesis of natural 8-and 9-membered lactones: Recent advancements in medium-sized ring formation [J].

Shiina, Isamu .

CHEMICAL REVIEWS, 2007, 107 (01) :239-273

[28] Evaluation of the Efficiency of the Macrolactonization Using MNBA in the Synthesis of Erythromycin A Aglycon [J].

Shiina, Isamu ;

Katoh, Takashi ;

Nagai, Shunsuke ;

Hashizume, Minako .

CHEMICAL RECORD, 2009, 9 (06) :305-320

[29] Kinetic Resolution of the Racemic 2-Hydroxyalkanoates Using the Enantioselective Mixed-Anhydride Method with Pivalic Anhydride and a Chiral Acyl-Transfer Catalyst [J].

Shiina, Isamu ;

Nakata, Kenya ;

Ono, Keisuke ;

Sugimoto, Masuhiro ;

Sekiguchi, Akihiro .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (01) :167-172

[30] 2,2-DISUBSTITUTED PROPIONIC ANHYDRIDES: EFFECTIVE COUPLING REAGENTS FOR THE KINETIC RESOLUTION OF SECONDARY BENZYLIC ALCOHOLS USING BTM [J].

Shiina, Isamu ;

Nakata, Kenya ;

Sugimoto, Masuhiro ;

Onda, Yu-suke ;

Iizumi, Takashi ;

Ono, Keisuke .

HETEROCYCLES, 2009, 77 (02) :801-810

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