REVERSAL OF REGIOSPECIFICITY IN THE KINETIC VS THERMODYNAMIC ENOLIZATION OF BICYCLIC KETONES - DIRECT BRIDGEHEAD FUNCTIONALIZATION OF THE BICYCLO[5.3.1]UNDECANE RING-SYSTEM

被引：25

作者：

SHEA, KJ

SAKATA, ST

机构：

[1] Department of Chemistry University of California, Irvine, Irvine

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(00)74233-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In contrast to aliphatic ketones, deprotonation of bicyclo [5.3.1] undecenone 3 gives the more highly substituted bridgehead enolate under conditions of kinetic control while the less highly substituted enolate is formed under conditions of thermodynamic control. These findings allow for the direct bridgehead functionalization of this important bicyclic skeleton.

引用

页码：4261 / 4264

页数：4

共 26 条

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