ASYMMETRIC-SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES USING THE AZA-DIELS-ALDER REACTION

被引：96

作者：

BAILEY, PD

BROWN, GR

KORBER, F

REED, A

WILSON, RD

机构：

[1] ICI PHARMACEUT PLC,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

[2] LIVERPOOL POLYTECH,DEPT BIOPHYS,LIVERPOOL L3 3AF,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)80025-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Imines of the type R-N=CHCO2Et can be coerced into undergoing a (4 + 2) cycloaddition with substituted dienes if the reaction is carried out in DMF in the presence of both water and acid; these reactions show extremely high regio- and diastereoselectivity. Use of the 1-phenylethyl group as a chiral auxiliary leads to moderate asymmetric induction (typical d.e. ca. 70%); moreover, the diastereoisomers are surprisingly easy to separate, giving a short general route to optically pure substituted pipecolic acid derivatives.

引用

页码：1263 / 1282

页数：20

共 69 条

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