A SULFINYL TRIALKOXYCARBONYL ETHENE AS A NEW ENANTIOPURE DIENOPHILE IN ASYMMETRIC DIELS-ALDER REACTIONS

被引：20

作者：

CARRETERO, JC

RUANO, JLG

CABREJAS, LMM

机构：

[1] Departamento de Química Orgánica, Universidad Autónoma Cantoblanco

来源：

TETRAHEDRON | 1995年 / 51卷 / 30期

关键词：

D O I：

10.1016/0040-4020(95)00443-C

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and the asymmetric Diels-Alder reactions of the enantiomerically pure (S)-p-tolylsulfinyl trialkoxycarbonyl ethene 3 with cyclic and acyclic dienes are reported. pi-Facial selectivity and regioselectivity are very high in all studied cases. Reactions with cyclopentadiene exhibit moderated or high exo-selectivity, which disappears with acyclic dienes. The use of high pressure improves the pi-facial selectivity but does not substantially modify the endo-exo selectivity.

引用

页码：8323 / 8332

页数：10

共 22 条

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