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
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
收藏
页码:6047 / 6049
页数:3
相关论文
共 36 条
[31]   CARBON-CARBON BOND FORMATION CATALYZED BY LITHIUM PERCHLORATE IN DICHLOROMETHANE [J].
REETZ, MT ;
FOX, DNA .
TETRAHEDRON LETTERS, 1993, 34 (07) :1119-1122
[32]   MICHAEL TYPE REACTION OF O-SILYLATED KETENE ACETALS WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS PROMOTED BY TITANIUM TETRACHLORIDE [J].
SAIGO, K ;
OSAKI, M ;
MUKAIYAMA, T .
CHEMISTRY LETTERS, 1976, (02) :163-164
[33]   ORGANOTIN TRIFLATE AS PRACTICAL CATALYST FOR MICHAEL ADDITION OF ENOL SILYL ETHERS [J].
SATO, T ;
WAKAHARA, Y ;
OTERA, J ;
NOZAKI, H .
TETRAHEDRON, 1991, 47 (47) :9773-9782
[34]   IMPORTANCE OF LEWIS ACID MEDIATED ELECTRON-TRANSFER IN MUKAIYAMA-MICHAEL REACTION OF KETENE SILYL ACETALS [J].
SATO, T ;
WAKAHARA, Y ;
OTERA, J ;
NOZAKI, H ;
FUKUZUMI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :4028-4030
[35]  
SATO T, 1991, TETRAHEDRON LETT, V21, P2405
[36]  
WEGHE PV, 1993, TETRAHEDRON LETT, V34, P3881