INTRAMOLECULAR DIELS-ALDER REACTIONS OF INTERNALLY-SUBSTITUTED TRIENYLSULFONES - SYNTHESIS OF BICYCLO[4.3.0] AND BICYCLO[4,4.0] SYSTEMS POSSESSING A BRIDGEHEAD SULFONYL GROUP

被引：15

作者：

CLASBY, MC ^{[1
]}

CRAIG, D ^{[1
]}

SLAWIN, AMZ ^{[1
]}

WHITE, AJP ^{[1
]}

WILLIAMS, DJ ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1995年 / 51卷 / 05期

关键词：

D O I：

10.1016/0040-4020(94)01045-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of trienes possessing internally-activated vinylic sulfone dienophilic groups undergo intramolecular Diels-Alder (IMDA) reaction with high or complete selectivity for the cis-fused products. Incorporation of silyloxy groups within the carbon tether linking the diene and dienophile results in increased IMDA reactivity. The stereochemical outcomes of these processes are rationalised in terms of the preference for an exooriented phenylsulfonyl group, and a minimisation of non-bonded interactions between the silyloxy and sulfone substituents.

引用

页码：1509 / 1532

页数：24

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