The Mukaiyama-Michael addition of a β,β-dimethyl substituted silyl ketene acetal to α,β-unsaturated ketones using tetra-n-butylammonium bibenzoate as a nucleophilic catalyst

被引：19

作者：

Gnaneshwar, R ^{[1
]}

Wadgaonkar, PP ^{[1
]}

Sivaram, S ^{[1
]}

机构：

[1] Natl Chem Lab, Div Polymer Chem, Pune 411008, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 32期

关键词：

Mukaiyama-Michael reactions; conjugate addition; 1,4-addition; delta-ketoester; O-silylated ketene acetal; alpha; beta-unsaturated ketones;

D O I：

10.1016/S0040-4039(03)01511-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Michael addition of a beta,beta-dimethyl substituted silyl ketene acetal [Me2C=C(OMe)OSiMe3] to alpha,beta-unsaturated ketones, namely, 2-cyclopentenone, 2-cyclohexenone, 3-methyl-2-cyclohexenone, isophorone, methyl vinyl ketone and mesityl oxide occurs smoothly in the presence of the nucleophilic catalyst, tetra-n-butyl ammonium bibenzoate (TBABB) in THE giving the corresponding 1,4-adducts in excellent yields. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：6047 / 6049

页数：3

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