Synthesis of tertiary cyclobutanols through stereoselective ring expansion of oxaspiropentanes induced by Grignard reagents

被引：16

作者：

Bernard, AM ^{[1
]}

Floris, C ^{[1
]}

Frongia, A ^{[1
]}

Piras, PP ^{[1
]}

机构：

[1] Univ Cagliari, Dipartimento Sci Chim, I-09042 Cagliari, Italy

来源：

TETRAHEDRON | 2000年 / 56卷 / 26期

关键词：

cyclopropanes; oxaspiropentanes; cyclobutanones; cyclobutanols; stereoselectivity; ring expansion; Grignard reagents;

D O I：

10.1016/S0040-4020(00)00369-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselectivity of the ring expansion of oxaspiropentanes to cyclobutanols induced by Grignard reagents has been studied. It has been found that the reaction occurs through the intermediacy of a cyclobutanone, formed stereospecifically, whereas the attack of the Grignard reagent on the carbonyl group of the cyclobutanone is stereospecific only in the case of the oxaspiropentanes derived from aldehydes. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4555 / 4563

页数：9

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