Reassignment of the absolute configuration of the baker's yeast reduction of (±)-ethyl 1-allyl-2-oxocyclopentanecarboxylate

被引：11

作者：

Allan, MM ^{[1
]}

Ramsden, PD ^{[1
]}

Burke, MJ ^{[1
]}

Parvez, M ^{[1
]}

Keay, BA ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 16期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0957-4166(99)00334-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The baker's yeast reduction of(+/-)-ethyl 1-allyl-2-oxocyclopentanecarboxylate under aqueous conditions in the presence of CuO yields (1S,2S)-(+)-ethyl 1-allyl-2-hydroxycyclopentanecarboxylate and the unreacted enantiomer (1R)-(-)-ethyl 1-allyl-2-oxocyclopentanecarboxylate. The absolute configuration of the secondary alcohol was determined from the X-ray crystal structure of the (1S)- 10-camphorsulfonyl derivative of (1S,2S)-(+)-ethyl 1-allyl-2-hydroxycyclopentanecarboxylate. This refutes configurational claims based on CD/ORD and chemical affiliation techniques currently reported in the literature for this reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：3099 / 3101

页数：3

共 19 条

[1] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE MICROBIAL REDUCTION OF CYCLIC ALPHA-ALKYL BETA-KETOESTERS [J].