MIGRATORY APTITUDE OF ALKYL SUBSTITUENTS IN THE MABR-PROMOTED EPOXIDE REARRANGEMENT

被引：48

作者：

MARUOKA, K ^{[1
]}

OOI, T ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] NAGOYA UNIV,DEPT APPL CHEM,CHIKUSA,NAGOYA 46401,JAPAN

来源：

TETRAHEDRON | 1992年 / 48卷 / 16期

关键词：

D O I：

10.1016/0040-4020(92)85006-Z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The migratory aptitude of the Lewis acid-promoted epoxide rearrangement has been studied with exceptionally bulky, Lewis acidic methylaluminum bis(4-bromo-2,6-di-tert-butylphenoxide) (MABR). With alpha,alpha-disubstituted epoxides, the organoaluminum-promoted epoxide rearrangement is interpreted for by proceeding with rigorous migration of hydride syn to the less hindered site of the epoxide ring, while the facile anti migration of the alkyl groups has been observed in tri- and tetrasubstituted epoxides. The selectivity observed in various types of epoxides is found to be far superior to that with other ordinary Lewis acids such as BF3.OEt2 and SnCl4.

引用

页码：3303 / 3312

页数：10

共 20 条

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