ORGANOTIN TRIFLATE AS PRACTICAL CATALYST FOR MICHAEL ADDITION OF ENOL SILYL ETHERS

被引：63
作者：
SATO, T
WAKAHARA, Y
OTERA, J
NOZAKI, H
机构：
[1] Department of Applied Chemistry, Okayama University of Science, Okayama, 700, Ridai-cho
来源：
TETRAHEDRON | 1991年 / 47卷 / 47期
关键词：
D O I：
10.1016/S0040-4020(01)80717-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Dibutyltin bis(triflate) is a mild Lewis acid which catalyzes clean Michael addition of enol silyl ethers. The new catalyst allows to employ various labile acceptors such as methyl vinyl ketone and 2-cyclopentenone which do not undergo smooth reaction with conventional Lewis acids. A variety of enol silyl ethers are also employable and thus 2-(trimethylsiloxy)propene, the simplest one in this class of compounds, can be used. The adducts of enol silyl ethers of cycloalkanones with vinyl ketones are readily cyclized to give the desired annulated enones free from isomers. Consequently, a practical version of the Robinson annulation has been realized.
引用
收藏
页码：9773 / 9782
页数：10
相关论文
共 76 条
[1]   KETENE ALKYLTRIALKYLSILYL ACETALS - SYNTHESIS, PRYOLYSIS AND NMR STUDIES [J].
AINSWORTH, C ;
CHEN, F ;
KUO, YN .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1972, 46 (01) :59-+
[2]  
[Anonymous], 1959, ORGANIC REACT
[3]   THERMAL-MICHAEL REACTION .4. MECHANISM [J].
AUSTIN, EM ;
BROWN, HL ;
BUCHANAN, GL ;
RAPHAEL, RA .
TETRAHEDRON, 1969, 25 (22) :5517-&
[4]   REGIOSPECIFICITY IN ENOLATE REACTIONS WITH ALPHA-SILYL VINYL KETONES - APPLICATION TO STEROID TOTAL SYNTHESIS [J].
BOECKMAN, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (19) :6179-6181
[5]   CONJUGATE ADDITION-ANNELATION - HIGHLY REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF POLYCYCLIC KETONES [J].
BOECKMAN, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (20) :6867-6869
[6]   HETEROGENEOUS CATALYSIS BY SALTS AND SOLVENTS .3. SYNTHESIS OF ALPHA, BETA-UNSATURATED CARBONYL-COMPOUNDS FROM SILYL ENOL ETHERS [J].
BOYER, J ;
CORRIU, RJP ;
PERZ, R ;
REYE, C .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 184 (02) :157-166
[7]   CYCLIC NITRONATES FROM THE DIASTEREOSELECTIVE ADDITION OF 1-TRIMETHYLSILYLOXYCYCLOHEXENE TO NITROOLEFINS - STARTING MATERIALS FOR STEREOSELECTIVE HENRY REACTIONS AND 1,3-DIPOLAR CYCLOADDITIONS [J].
BROOK, MA ;
SEEBACH, D .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (04) :836-850
[8]   ORGANIC-REACTIONS AT HIGH-PRESSURE - CONJUGATE ADDITIONS OF O-SILYLATED KETENE ACETALS TO ACTIVATED ENONES [J].
BUNCE, RA ;
SCHLECHT, MF ;
DAUBEN, WG ;
HEATHCOCK, CH .
TETRAHEDRON LETTERS, 1983, 24 (45) :4943-4946
[9]  
Chapdelaine M.J., 1990, ORGANIC REACTIONS, P225
[10]  
DAUBEN HJ, 1960, J ORG CHEM, V25, P1442
12345678