CONJUGATE ADDITION-REACTIONS OF CHIRAL (E)-CROTYLSILANES - APPLICATION TO AN ASYMMETRIC [3+2] CYCLOPENTANE ANNULATION

被引：76
|
作者：
PANEK, JS
JAIN, NF
机构：
[1] Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 09期
关键词：
D O I：
10.1021/jo00061a001
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Functionalized (E)-crotylsilanes 1 undergo Lewis acid promoted conjugate addition reactions with alpha-substituted enals and methyl vinyl ketone 2 to produce tetrasubstituted cyclopentanes 3 with high levels of diastereoselection. The reaction is believed to proceed by an initial 1,4-addition which is followed by a 1,2-silyl migration and a final cyclization step involving the derived boron enolate resulting in the construction of the cyclopentanoid product.
引用
收藏
页码：2345 / 2348
页数：4
相关论文
共 50 条
12345