Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries

被引：20

作者：

Banks, MR

Blake, AJ

Cadogan, JIG

Doyle, AA

Gosney, I

Hodgson, PKG

Thorburn, P

机构：

[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

[2] BP INT LTD,RES & ENGN CTR,SUNBURY TW16 7LN,MIDDX,ENGLAND

来源：

TETRAHEDRON | 1996年 / 52卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(96)00070-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Transposition of the dormant methyl group from C-1 in chiral oxazolidin-2-one 2 to C-7 in a six step synthetic sequence from (1R)-camphor 5 creates a novel transfigomer 4 with sufficient pi-topological bias to induce excellent levels of asymmetric induction in Lewis-acid catalysed Diels-Alder reactions of its alpha,beta-unsaturated carboximide derivatives with cyclopentadiene. Further modification of 4 by replacement of the C-7 methyl group with an ethyl substituent raises the level of diastereoselectivity for the acrylate derivative 11a from 81 to >95% d.e..

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页码：4079 / 4094

页数：16

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