Reductive aldol reactions on aromatic heterocycles

被引：10

作者：

Donohoe, TJ

Ace, KW

Guyo, PM

Helliwell, M

McKenna, J

机构：

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

[2] Rhone Poulenc Rorer, Dagenham Res Ctr, Dagenham RM10 3RX, England

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

birch reduction; aldol; pyrrole; furan;

D O I：

10.1016/S0040-4039(99)02224-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn-aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：989 / 993

页数：5

共 9 条

[1] Stereoselectivity in the birch reduction of 2-furoic acid derivatives [J].