Reaction of optically active α-aminoallenylstannanes with aldehydes formed in situ from the lewis-acid-catalyzed rearrangement of epoxides

被引：14

作者：

de los Ríos, C ^{[1
]}

Hegedus, LS ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 16期

关键词：

D O I：

10.1021/jo050813b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of optically active alpha-oxazolidinonylallenylstannanes with oxiranes in the presence of BF3 center dot OEt2 produced beta-hydroxypropargylamines with high syn diastereoselectivity and high enantioselectivity through an initial Lewis-acid-catalyzed rearrangement of the oxirane to the corresponding aldehyde via an alkyl, aryl, or hydride shift. This permits the use of readily available oxiranes as alternatives to aldehydes that are difficult to prepare and/or unstable.

引用

页码：6541 / 6543

页数：3

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