Reexamination of the traditional Baylis-Hillman reaction

被引：24

作者：

Shi, M ^{[1
]}

Li, CQ ^{[1
]}

Jiang, JK ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Organomet Chem Lab, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2003年 / 59卷 / 08期

关键词：

Baylis-Hillman reaction; Lewis base; methyl vinyl ketone (MVK); ethyl vinyl ketone (EVK); DABCO; conjugated addition; DMAP;

D O I：

10.1016/S0040-4020(03)00041-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone (MVK), we found that, besides the normal Baylis-Ellman adduct 1, the diadduct 2 can also be formed at the same time and the yield of 2 can reach to 55% if increasing the amount of methyl vinyl ketone. But for ethyl vinyl ketone (EVK), methyl acrylate or acrylonitrile, only the normal Baylis-Hillman adduct 4, 7 or 8 was obtained, respectively. The substituent's effects and Lewis base effects were also examined and a plausible reaction mechanism was proposed for the formation of 2. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1181 / 1189

页数：9

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