CYCLOADDITIONS OF ALLYLSILANES .6. LEWIS-ACID PROMOTED [2+2] CYCLOADDITION OF ALLYLSILANES AND UNSATURATED ESTERS - A NOVEL METHOD FOR CYCLOBUTANE CONSTRUCTION

被引:58
作者
KNOLKER, HJ [1 ]
BAUM, G [1 ]
GRAF, R [1 ]
机构
[1] UNIV KARLSRUHE,INST ANORGAN CHEM,D-76131 KARLSRUHE,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 15-16期
关键词
D O I
10.1002/anie.199416121
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A third mode of reactivity for allylsilanes in their reactions with α,β‐unsaturated carbonyl compounds has been found in addition to the Sakurai reaction and the [3 + 2] cycloaddition. Silylmethyl‐cyclobutanes are formed regioselectively via a siliranium ion intermediate (1). The reaction with methyl propynoate provides bicyclo[2.2.0]hexanes in a one‐pot conversion. (Figure Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
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页码:1612 / 1615
页数:4
相关论文
共 48 条
[1]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[2]   STEREOCHEMISTRY OF THE SAKURAI REACTION - ADDITIONS TO CYCLOHEXENONES AND CYCLOHEPTENONES [J].
BLUMENKOPF, TA ;
HEATHCOCK, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2354-2358
[3]   5-MEMBERED RING ANNULATION VIA PROPARGYLSILANES AND ALLYLSILANES [J].
DANHEISER, RL ;
DIXON, BR ;
GLEASON, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6094-6097
[4]   STEREOCHEMICAL COURSE OF THE ALLYSILANE BASED CYCLOPENTANE ANNULATION [J].
DANHEISER, RL ;
TAKAHASHI, T ;
BERTOK, B ;
DIXON, BR .
TETRAHEDRON LETTERS, 1993, 34 (24) :3845-3848
[5]   REGIOSPECIFIC MICHAEL REACTIONS TO AN ENEDIONE [J].
DANISHEFSKY, S ;
KAHN, M .
TETRAHEDRON LETTERS, 1981, 22 (06) :485-488
[6]  
Hanstein W., 1970, J AM CHEM SOC, V92, P829
[7]  
HARTMAN GD, 1975, TETRAHEDRON LETT, P939
[8]   NEW ACCESS TO DI-EXO-METHYLENECYCLOBUTANES VIA [2+2] CYCLOADDITION OF 3-METHYLTHIO-4-TRIMETHYLSILYL-1,2-BUTADIENE WITH ALKENES MEDIATED BY A LEWIS-ACID [J].
HOJO, M ;
TOMITA, K ;
HIROHARA, Y ;
HOSOMI, A .
TETRAHEDRON LETTERS, 1993, 34 (50) :8123-8126
[9]   LATENT ACETONYLATION OF ALPHA,BETA-ENONES WITH ALLYLTRIMETHYLSILANE OR 2-METHYL-2-PROPENYLTRIMETHYLSILANE - SYNTHESIS OF 1,5-DIKETONES AND ANNELATION TO FUSED CYCLOHEXENONES [J].
HOSOMI, A ;
KOBAYASHI, H ;
SAKURAI, H .
TETRAHEDRON LETTERS, 1980, 21 (10) :955-958
[10]   CHEMISTRY OF ORGANOSILICON COMPOUNDS .99. CONJUGATE ADDITION OF ALLYLSILANES TO ALPHA, BETA-ENONES - NEW METHOD OF STEREOSELECTIVE INTRODUCTION OF ANGULAR ALLYL GROUP IN FUSED CYCLIC ALPHA, BETA-ENONES [J].
HOSOMI, A ;
SAKURAI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) :1673-1675