Synthesis of alicyclic esters via an intramolecular conjugate addition reaction.: New method for generating (Z)-vinylcopper species from 1,1-dibromoalkenes

被引：28

作者：

Tanino, K ^{[1
]}

Arakawa, K ^{[1
]}

Satoh, M ^{[1
]}

Iwata, Y ^{[1
]}

Miyashita, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 06期

关键词：

cyclobutanone; organocopper; conjugate addition; cyclization; dihaloalkene;

D O I：

10.1016/j.tetlet.2005.12.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel cyclization reaction of a 1,1-dibromoalkene derivative having an alpha,beta-unsaturated ester moiety was developed. Under the influence of Me2CuLi, the 1,1-dibromoalkene was converted into a (Z)-vinylcopper species which in turn underwent an intramolecular conjugate addition reaction with the alpha,beta-unsaturated ester moiety. Five-, six-, and seven-membered carbocycles were constructed by the present method. The substrate having an epoxide moiety also afforded a five-membered product via a 5-exo type intramolecular cyclization reaction. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：861 / 864

页数：4

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