Regio- and stereoselective C-2 and C-3 cleavage of 2-(1-aminoalkyl)aziridines with alcohols, carboxylic acids, and sodium iodide

被引：19

作者：

Concellón, JM ^{[1
]}

Riego, E ^{[1
]}

Suárez, JR ^{[1
]}

机构：

[1] Univ Oviedo, Fac Quim, Dept Quim Organ & Inorgan, E-33071 Oviedo, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 24期

关键词：

D O I：

10.1021/jo0350514

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring opening of nonactivated aziridines 1 using several nucleophiles, such as alcohols, carboxylic acids, and sodium iodide, is described. Depending on the nucleophile used, aziridines 1 are cleaved at C-3 or C-2 with total regio- and stereoselectivity, affording chiral 2-alkoxy-1,3-diamines 2 with alcohols, or O-acylated-1-hydroxy-2,3-diamines 6 with carboxylic acids in moderate or high yield. In the case of the aziridines derived from phenylalanine, treatment with NaI afford trans-4-phenylbut-3-en-1,2-diamines 9, generating the alkene with total diastereoselectivity. Mechanisms have been proposed to explain these reactions.

引用

页码：9242 / 9246

页数：5

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