Tandem formation and [2,3] rearrangement of methylene ammonium ylides derived from amines and the Simmons-Smith reagent

被引：27

作者：

Aggarwal, VK ^{[1
]}

Fang, GY

Charmant, JPH

Meek, G

机构：

[1] Univ Bristol, Dept Chem, Bristol, Avon, England

[2] Dowpharma Chirotech Technol Ltd, Cambridge, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 10期

关键词：

D O I：

10.1021/ol034404i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Zinc-complexed methylene ammonium ylides are formed from tertiary amines and the Simmons-Smith reagent. These stable entities can be activated with n-BuLi to allow reactions typical of ammonium ylides such as [2,3] rearrangements. In the case of oxazolidine 12, ylide formation, activation, and subsequent [2,3] rearrangement was highly efficient and occurred with very high diastereoselectivity.

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页码：1757 / 1760

页数：4

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