The stereoselective birch reduction of pyrroles

被引：21

作者：

Donohoe, TJ ^{[1
]}

Guyo, PM ^{[1
]}

Helliwell, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 03期

关键词：

D O I：

10.1016/S0040-4039(98)02395-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Birch reduction has been applied to electron-deficient pyrroles substituted with a chiral auxiliary at the C-2 position. Using either 8-phenylmenthol or trans-2-(alpha-cumyl)cyclohexanol (TCC) as auxiliaries, high levels of stereoselectivity were obtained. Moreover, the auxiliary could be removed using a high-yielding three-step sequence to furnish substituted dehydroproline derivatives with high enantiomeric purity. By choosing either (-)-8-phenylmenthol or (+)-TCC as an auxiliary either enantiomer of the dehydroproline product could be obtained. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：435 / 438

页数：4

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