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

[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] 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

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

Birman, Vladimir B. ;

Li, Ximin ;

Han, Zhenfu .

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

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

Birman, Vladimir B. ;

Guo, Lei .

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

[6] 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

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

Fu, GC .

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

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

Fu, GC .

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

[9] 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

[10] Enantioselective addition of amines to ketenes catalyzed by a planar-chiral derivative of PPY: Possible intervention of chiral Bronsted-acid catalysis [J].

Hodous, BL ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :10006-10007

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