Enantio- and regiospecific reduction of ethyl 4-phenyl-2.4-dioxobutyrate with baker's yeast:: preparation of (R)-HPB ester

被引：50

作者：

Fadnavis, NW ^{[1
]}

Radhika, KR ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Biotransformat Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 21期

关键词：

D O I：

10.1016/j.tetasy.2004.09.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 [无机化学]; 081704 [应用化学];

摘要：

Ethyl 2,4-dioxo-4-phenylbutyrate obtained by condensation of acetophenone with diethyl oxalate is reduced enantio- and regiospecifically by baker's yeast in a diisopropyl ether/water two-phase system to give (-)-ethyl (R)-2-hydroxy-4-oxo-4-phenylbutyrate with an ee = 98% in 80% isolated yield. The hydroxyester was hydrogenated over Pd-C to obtain (-)-ethyl (R)-2-hydroxy-4-phenylbutyrate (HPB ester), an important intermediate for the synthesis of ACE inhibitors. Prolonged contact of the reduction product with baker's yeast produced 3-phenyl 3-oxo propanol in 90% yield. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3443 / 3447

页数：5

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