Regio- and stereospecific cleavage of alpha,beta-epoxysilanes with lithium diphenylphosphide

被引:14
作者
Cuadrado, P [1 ]
GonzalezNogal, AM [1 ]
机构
[1] UNIV VALLADOLID,DEPT QUIM ORGAN,E-47011 VALLADOLID,SPAIN
关键词
D O I
10.1016/S0040-4039(97)10123-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Silyl epoxides In-e react with lithium diphenylphosphide and then with methyl iodide to give vinylphosphonium iodides resulting from alpha-opening of the epoxide ring and subsequent Peterson elimination. In the same conditions, the E-beta-phenyl-alpha-tert-butyldiphenylsilylepoxide If leads to the corresponding silyl enol ether 5 by beta-opening followed by Brook rearrangement. Both processes are regio-and stereospecific. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8117 / 8120
页数:4
相关论文
共 18 条
[11]  
HUDRLIK PF, 1979, TETRAHEDRON LETT, P2233
[12]  
HUDRLIK PF, 1974, TETRAHEDRON LETT, P1133
[13]   STEREOSPECIFIC SYNTHESIS OF HETEROATOM-SUBSTITUTED OLEFINS FROM ALPHA,BETA-EPOXYSILANES - PREPARATION OF VINYL BROMIDES, ENOL ACETATES, ENOL ETHERS, AND ENAMIDES [J].
HUDRLIK, PF ;
HUDRLIK, AM ;
RONA, RJ ;
MISRA, RN ;
WITHERS, GP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) :1993-1996
[14]   REACTIONS OF ALPHA,BETA-EPOXYSILANES WITH ORGANOCUPRATE REAGENTS - NEW STEREOSPECIFIC OLEFIN SYNTHESIS [J].
HUDRLIK, PF ;
PETERSON, D ;
RONA, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) :2263-2264
[15]   STEREOSPECIFIC OLEFIN-FORMING ELIMINATION-REACTIONS OF BETA-HYDROXYALKYLSILANES [J].
HUDRLIK, PF ;
PETERSON, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (06) :1464-1468
[16]   CONVENIENT PREPARATION OF TRIISOPROPYLSILYL ACYL SILANES [J].
LIPSHUTZ, BH ;
LINDSLEY, C ;
SUSFALK, R ;
GROSS, T .
TETRAHEDRON LETTERS, 1994, 35 (48) :8999-9002
[17]  
Weber W. P., 1983, SILICON REAGENTS ORG, P206
[18]  
ZBIRAL E, 1979, ORGANOPHOSPHORUS REA, P223