ASYMMETRIC INTERMOLECULAR DIELS-ALDER REACTIONS OF ENANTIOPURE SULFINYL-HOMODIENES AND SULFINYL-HETERODIENES - PRELIMINARY-RESULTS

被引：39

作者：

GOSSELIN, P

BONFAND, E

HAYES, P

RETOUX, R

MAIGNAN, C

机构：

[1] FAC SCI LE MANS,SYNTH ORGAN LAB,CNRS,URA 482,F-72017 LE MANS,FRANCE

[2] FAC SCI LE MANS,FLUORURES LAB,CNRS,URA 449,F-72017 LE MANS,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(00)86226-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reaction of (E)-(+)-(R)-2-p-tolylsulfinyl-1,3-pentadiene 1 with maleimide afforded 3 as a single, enantiomerically pure adduct under very mild conditions. 3 resulted from exclusive endo approach by a completely diastereofacialselective route. On the other hand, heterodiene (+)-(S)-3-p-tolylsulfinyl-3-buten-2-one 2 smoothly reacted with sensitive 2-methylenetetrahydrofuran yielding 1:1 diastereomeric dioxaspirodducts 4a and 4b, readily separated by liquid chromatography.

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页码：781 / 784

页数：4

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