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

被引：109

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

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