Stereoselectivity in the birch reduction of 2-furoic acid derivatives

被引：26

作者：

Donohoe, TJ ^{[1
]}

Helliwell, M ^{[1
]}

Stevenson, CA ^{[1
]}

Ladduwahetty, T ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(98)00361-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation and Birch reduction of chiral 3-methyl-2-furoic acid derivatives is described. Using a C-2 symmetrical amine as a chiral auxiliary, very high levels of stereochemical control could be obtained. Moreover, the auxiliary could be removed conveniently by heating in 6M HCl to liberate a carboxylic acid of high enantiomeric purity. The relative stereochemistry of the Birch reduced amides (and therefore the absolute stereochemistry of the corresponding acids) was determined unambiguously from an X-ray crystal structure. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3071 / 3074

页数：4

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