Stereoselective Grignard reactions to alpha-amino nitrones. Synthesis of optically active alpha-aminohydroxylamines and 1,2-diamines

被引：49

作者：

Merino, P

Lanaspa, A

Merchan, FL

Tejero, T

机构：

[1] Depto. de Quim. Orgánica, ICMA, Universidad de Zaragoza

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 14期

关键词：

D O I：

10.1016/S0957-4166(97)00250-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

alpha-Aminohydroxylamines are formed stereoselectively from the nucleophilic addition of phenylmagnesium bromide to cr-amino nitrones. In contrast, the addition of methylmagnesium bromide occurs in a stereorandom fashion. Nevertheless it is possible to achieve a complete syn selectivity by diprotecting the alpha-amino group in the starting nitrone. Hydrogenation of the obtained alpha-amino hydroxylamines followed by deprotection of the tert-butoxycarbonyl group affords optically active 1,2-diamines. (C) 1997 Elsevier Science Ltd.

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页码：2381 / 2401

页数：21

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