Functionalised allylsilanes from silylcopper reagents and allene.: A useful strategy for cyclopentane annulations

被引:44
作者
Barbero, A [1 ]
García, C [1 ]
Pulido, FJ [1 ]
机构
[1] Univ Valladolid, Dept Quim Organ, E-47011 Valladolid, Spain
关键词
silylcupration; allene; allylsilane; cyclization;
D O I
10.1016/S0040-4020(00)00129-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Silylcupration of allene using phenyldimethylsilylcopper or t-butyldiphenylsilylcopper followed by reaction with alpha,beta-unsaturated acyl chlorides, aldehydes or ketones affords allylsilane-containing divinyl ketones and oxoallylsilanes, respectively. They undergo highly stereocontrolled silicon-assisted intramolecular cyclizations when treated with protic or Lewis acid leading to cyclopentane ring-formation. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2739 / 2751
页数:13
相关论文
共 46 条
[1]   INSERTION OF ETHYLENE INTO ZR-SI AND HF-SI BONDS [J].
ARNOLD, J ;
ENGELER, MP ;
ELSNER, FH ;
HEYN, RH ;
TILLEY, TD .
ORGANOMETALLICS, 1989, 8 (09) :2284-2286
[2]   SYNTHESIS OF ALLYSTANNANES AND VINYLSTANNANES BY THE STANNYL-CUPRATION OF ALLENES [J].
BARBERO, A ;
CUADRADO, P ;
FLEMING, I ;
GONZALEZ, AM ;
PULIDO, FJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (03) :327-331
[3]   SYNTHESIS OF VINYLSILANES BY SILYL-CUPRATION OF ACETYLENES USING TERT-BUTYLDIPHENYLSILYL-CUPRATE REAGENTS [J].
BARBERO, A ;
CUADRADO, P ;
FLEMING, I ;
GONZALEZ, AM ;
PULIDO, FJ ;
SANCHEZ, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (12) :1525-1532
[4]   Stannylcupration of acetylenes followed by reaction with epoxides:: A novel annulation strategy for the synthesis of cyclobutenes [J].
Barbero, A ;
Cuadrado, P ;
García, C ;
Rincón, JA ;
Pulido, FJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7531-7533
[5]   RING-FORMATION FROM ALLYLSTANNANES AND VINYLSTANNANES INITIATED BY TREATMENT WITH BUTYL-LITHIUM [J].
BARBERO, A ;
CUADRADO, P ;
GONZALEZ, AM ;
PULIDO, FJ ;
RUBIO, R ;
FLEMING, I .
TETRAHEDRON LETTERS, 1992, 33 (39) :5841-5842
[6]   THE SYNTHESIS OF ALLYLSTANNANES AND VINYLSTANNANES BY THE STANNYL-CUPRATION OF ALLENES [J].
BARBERO, A ;
CUADRADO, P ;
FLEMING, I ;
GONZALEZ, AM ;
PULIDO, FJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (15) :1030-1031
[7]   THE REACTION OF TERT-BUTYLDIPHENYLSILYCUPRATES WITH ALLENES [J].
BARBERO, A ;
CUADRADO, P ;
GONZALEZ, AM ;
PULIDO, FJ ;
FLEMING, I .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (11) :2811-2816
[8]   Silylcupration of allenes followed by reaction with enones.: A new strategy for the synthesis of methylenecyclopentanols [J].
Barbero, A ;
García, C ;
Pulido, FJ .
TETRAHEDRON LETTERS, 1999, 40 (36) :6649-6652
[9]   STANNYL-CUPRATION OF ACETYLENES AND THE REACTION OF THE INTERMEDIATE CUPRATES WITH ELECTROPHILES AS A SYNTHESIS OF SUBSTITUTED VINYLSTANNANES [J].
BARBERO, A ;
CUADRADO, P ;
FLEMING, I ;
GONZALEZ, AM ;
PULIDO, FJ ;
RUBIO, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (14) :1657-1662
[10]   THE STANNYL CUPRATION OF ACETYLENES AND THE REACTION OF THE INTERMEDIATE CUPRATES WITH ELECTROPHILES AS A SYNTHESIS OF SUBSTITUTED VINYLSTANNANES [J].
BARBERO, A ;
CUADRADO, P ;
FLEMING, I ;
GONZALEZ, AM ;
PULIDO, FJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :351-353