Kinetic Resolution of Racemic Carboxylic Acids Using Achiral Alcohols by the Promotion of Benzoic Anhydrides and Tetramisole Derivatives: Production of Chiral Nonsteroidal Anti-Inflammatory Drugs and Their Esters

被引：61

作者：

Shiina, Isamu ^{[1
]}

Nakata, Kenya ^{[1
]}

Onda, Yu-suke ^{[1
]}

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 35期

关键词：

Kinetic resolution; Carboxylic acids; Anhydrides;

D O I：

10.1002/ejoc.200800942

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of optically active carboxylic esters were produced by kinetic resolution of racemic carboxylic acids by using achiral alcohols, benzoic anhydrides, and Birman's tetramisole-type catalysts. Bis(alpha-naphthyl)methanol is a very effective reagent for producing the corresponding esters with high ee values in the presence of 4-methoxybenzoic anhydride (PMBA) as the coupling reagent by promotion of benzotetramisole derivatives (BTM, alpha-Np-BTM, and beta-Np-BTM). This protocol directly provides chiral carboxylic esters from free carboxylic acids and achiral alcohols by utilizing a transacylation process to generate the mixed anhydrides from the acid components with benzoic anhydride derivatives in the presence of chiral catalysts. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

引用

页码：5887 / 5890

页数：4

共 22 条

[1] Benzotetramisole: A remarkably enantioselective acyl transfer catalyst [J].

Birman, VB ;

Li, XM .

ORGANIC LETTERS, 2006, 8 (07) :1351-1354

[2] Influence of electronic and steric factors on 2,3-dihydroimidazo [1,2-a]pyridine-based enantioselective acylation catalysts [J].

Birman, VB ;

Li, XM ;

Jiang, H ;

Uffman, EW .

TETRAHEDRON, 2006, 62 (2-3) :285-294

[3] Kinetic resolution of alcohols using a 1,2-dihydroimidazo[1,2-a]quinoline enantioselective acylation catalyst [J].

Birman, VB ;

Jiang, H .

ORGANIC LETTERS, 2005, 7 (16) :3445-3447

[4] 2,3-dihydroimidazo[1,2-a]pyridines: A new class of enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols [J].

Birman, VB ;

Uffman, EW ;

Hui, J ;

Li, XM ;

Kilbane, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12226-12227

[5] Nonaromatic amidine derivatives as acylation catalysts [J].

Birman, Vladimir B. ;

Li, Ximin ;

Han, Zhenfu .

ORGANIC LETTERS, 2007, 9 (01) :37-40

[6] Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole [J].

Birman, Vladimir B. ;

Guo, Lei .

ORGANIC LETTERS, 2006, 8 (21) :4859-4861

[7] Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation [J].

Birman, Vladimir B. ;

Jiang, Hui ;

Li, Ximin ;

Guo, Lei ;

Uffman, Eric W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (20) :6536-6537

[8] Enantioselective nucleophilic catalysis with "planar-chiral" heterocycles [J].

Fu, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :412-420

[9] Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine [J].

Fu, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :542-547

[10] Enantioselective addition of alcohols to ketenes catalyzed by a planar-chiral azaferrocene: Catalytic asymmetric synthesis of arylpropionic acids [J].

Hodous, BL ;

Ruble, JC ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2637-2638

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