Cp2TiCl-promoted isomerization of trisubstituted epoxides to exo-methylene allylic alcohols on carvone derivatives

被引：35

作者：

Bermejo, F ^{[1
]}

Sandoval, C ^{[1
]}

机构：

[1] Univ Salamanca, Fac Ciencias Quim, Dept Quim Organ, E-37008 Salamanca, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 16期

关键词：

D O I：

10.1021/jo049358u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ring-opening reaction of trisubstituted epoxides promoted by Cp2TiCl led to exo-methylene allylic alcohols as major compounds when 0.5 M solutions of the epoxides were added to 0.1 M solutions of the reagent at room temperature in THF. In most cases, the allylic alcohols were contaminated with saturated alcohols. Normal and reverse addition modes led to the alternate product being favored. The different stereochemical outcome of cis- and trans-epoxy acetates is rationalized in terms of mechanistically biased elimination processes.

引用

页码：5275 / 5280

页数：6

共 31 条

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