Aluminum amalgam for the reduction of sensitive β-nitroamines to 1,2-diamines

被引：20

作者：

Anderson, James C. ^{[1
]}

Chapman, Helen A. ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

SYNTHESIS-STUTTGART | 2006年 / 19期

关键词：

reduction; aluminum; amines; beta-nitroamine; 1,2-diamine;

D O I：

10.1055/s-2006-950229

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A two-step reduction protocol for the conversion of a range of sensitive beta-nitroamines to 1,2-diarnines has been developed that is operationally simpler, cheaper and higher-yielding than the previously reported SmI2 protocol. Reduction of the nitro function to a hydroxylamine was achieved with Al amalgam and then reduced to the 1,2-diamine product with H-2, Pd/C or LiAlH4 with no erosion of diastereoselectivity. A representative selection of 9 beta-nitroamines were reduced in 71-94% yield.

引用

页码：3309 / 3315

页数：7

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