REGIO-SELECTIVE AND STEREOSELECTIVE SYNTHESIS OF 1,2-DISUBSTITUTED VINYLSILANES

被引:20
作者
OBAYASHI, M [1 ]
UTIMOTO, K [1 ]
NOZAKI, H [1 ]
机构
[1] KYOTO UNIV,DEPT IND CHEM,KYOTO 606,JAPAN
关键词
D O I
10.1016/S0022-328X(00)92339-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The alkylcopper reagents prepared from RMgBr and CuBr react with trimethylsilylacetylene to give regio- and stereo-selectivity 1-trimethylsilyl-1(Z)-alkenylcopper adducts. Hydrolysis affords 1-trimethylsilyl-1(E)-alkenes exclusively. Alkylation, acylation, halogenation, and stannylation proceed stereoselectively to afford synthetically useful intermediates. Homopropargylation of alkyl 1-trimethylsilyl-1(Z)-alkenylcuprates provided better yield than that of the original vinylcopper reagents. © 1979.
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页码:145 / 152
页数:8
相关论文
共 34 条
[1]   STEREOCHEMISTRY OF ADDITION OF SILICOCHLOROFORM TO ACETYLENES - A COMPARISON OF CATALYST SYSTEMS [J].
BENKESER, RA ;
BURROUS, ML ;
SWISHER, JV ;
NELSON, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (21) :4385-&
[2]  
CHAN TH, 1974, TETRAHEDRON LETT, P171
[3]   SYNTHESIS OF ALKENES FROM CARBONYL-COMPOUNDS AND CARBANIONS ALPHA TO SILICON .4. STEREOSELECTIVE CONVERSION OF RCHO INTO E-RCH-]CHCH2CL [J].
CHAN, TH ;
MYCHAJLOWSKIJ, W ;
ONG, BS ;
HARPP, DN .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 107 (01) :C1-C4
[4]   SILICON IN ORGANIC-SYNTHESIS [J].
COLVIN, EW .
CHEMICAL SOCIETY REVIEWS, 1978, 7 (01) :15-64
[5]   MECHANISM OF SOLVOLYSIS OF (2-BROMOETHYL)TRIMETHYLSILANE - EVIDENCE FOR MIGRATION OF TRIMETHYLSILYL GROUP [J].
COOK, MA ;
EABORN, C ;
WALTON, DRM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1970, 24 (02) :301-&
[6]   ORGANOMETALLIC COMPOUNDS OF GROUP 3 .36. REGIOSPECIFIC AND STEREOSELECTIVE CARBOMETALLATION OF ALKYNYLSILANES BY ZIEGLER-NATTA ALKYLATING-AGENTS [J].
EISCH, JJ ;
MANFRE, RJ ;
KOMAR, DA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 159 (04) :C13-C19
[7]   ORGANOMETALLIC COMPOUNDS OF GROUP-3 .35. STEREOSPECIFIC REDUCTIVE ALKYLATION OF ACETYLENES BY SUCCESSIVE HYDRALUMINATION AND CARBODEMETALLATION [J].
EISCH, JJ ;
DAMASEVITZ, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (12) :2214-2215
[8]  
FLEMING I, 1975, CHEM IND-LONDON, P449
[9]   GENERATION AND REACTIONS OF ALPHA-(TRIMETHYLSILYL)-, ALPHA-(PHENYLTHIO)-, AND ALPHA-(PHENYLSELENO)VINYLLITHIUM DERIVATIVES1,2) [J].
GROBEL, BT ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (03) :867-877
[10]  
HUDRLIK PF, 1976, J ORGANOMETAL CHEM L, V1, P127