Efficient preparation of an N-aryl β-amino acid via asymmetric hydrogenation and direct asymmetric reductive amination en route to Ezetimibe

被引：31

作者：

Busscher, Guuske F. ^{[1
]}

Lefort, Laurent ^{[1
]}

Cremers, Jozef G. O. ^{[1
]}

Mottinelli, Marco ^{[1
]}

Wiertz, Roel W. ^{[1
]}

de Lange, Ben ^{[1
]}

Okamura, Yutaka ^{[2
]}

Yusa, Yukinori ^{[2
]}

Matsumura, Kazuhiko ^{[2
]}

Shimizu, Hideo ^{[2
]}

de Vries, Johannes G. ^{[1
]}

de Vries, Andre H. M. ^{[1
]}

机构：

[1] DSM Innovat Synth BV, Unit DSM Pharma Chem, NL-6160 MD Geleen, Netherlands

[2] Takasago Int Corp, Corp Res & Dev Div, Hiratsuka, Kanagawa 2540073, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 13-14期

关键词：

CATALYZED COUPLING REACTION; ENANTIOSELECTIVE SYNTHESIS; CHOLESTEROL ABSORPTION; ALPHA-AMINO; ENAMINES; HALIDES; DERIVATIVES; ESTERS; LIBRARIES;

D O I：

10.1016/j.tetasy.2010.04.013

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two routes for the preparation of an N-aryl beta-amino acid, an important precursor for the cholesterol-lowering drug Ezetimibe, were investigated. The first pathway proceeds via an Rh- or Ir-catalyzed asymmetric hydrogenation of N-aryl enamine giving the desired product with up to 82% ee. The other pathway involves a direct asymmetric reductive amination (DARA) of the beta-keto ester which yielded the beta-amino ester in high yield and 97% ee. Subsequent copper-catalyzed N-arylation gave the target compound. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1709 / 1714

页数：6

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