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
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
收藏
页码:8323 / 8332
页数:10
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