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
收藏
页码：1181 / 1189
页数：9
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