HETEROATOM-ASSISTED ISOMERIZATION OF OXIRANES TO ALLYLIC ALCOHOLS PROMOTED BY BASES

被引：31

作者：

MORDINI, A

PECCHI, S

CAPOZZI, G

CAPPERUCCI, A

DEGL'INNOCENTI, A

REGINATO, G

RICCI, A

机构：

[1] DIPARTIMENTO CHIM, I-85100 POTENZA, ITALY

[2] DIPARTIMENTO CHIM ORGAN A MANGINI, I-40136 BOLOGNA, ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 17期

关键词：

D O I：

10.1021/jo00096a020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The isomerization of alkoxy-substituted oxiranes to hydroxy-substituted ene ethers promoted by mixed metal bases has been investigated. The structure of the oxirane substrate (the number, the position, and the type of alkyl substituents on the ring) plays an important role in driving the stereoselectivity of the reaction. Disubstituted oxiranes show a predictable preference for the E-ene ether while trisubstituted substrates give either a mixture of stereoisomers or the E-ene ether exclusively, depending on the location of the third alkyl substituent.

引用

页码：4784 / 4790

页数：7

共 32 条

[1]

BESSIERE.Y, 1971, B SOC CHIM FR, P4391

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