(S)-(+)-3-p-tolylsulfinylbut-3-en-2-one: A spectacular oxabutadiene for asymmetric cycloaddition of styrenic compounds

被引：26

作者：

Hayes, P ^{[1
]}

Dujardin, G ^{[1
]}

Maignan, C ^{[1
]}

机构：

[1] UNIV MAINE,CNRS,SYNTH ORGAN LAB,F-72017 LE MANS,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 21期

关键词：

D O I：

10.1016/0040-4039(96)00619-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heterocycloaddition of optically active (S)-(+)-3-p-tolylsulfinylbut-3-en-2-one 1 was successfully achieved with various electron-rich dienophiles in extremely mild and noncatalytic conditions. Nature of the dienophile (enol ether 2 v.s. styrene 3) proved to play a critical role in the stereochemical outcome of the reaction : less than 14% de with 2, more than 94% de with 3. Copyright (C) 1996 Published by Elsevier Science Ltd.

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页码：3687 / 3690

页数：4

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