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

页码：2345 / 2348

页数：4

共 30 条

[1]

Birkofer L., 1989, CHEM ORGANIC SILICON

[2]

BROOK AG, 1980, REARRANGEMENTS GROUN, V2, P190

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