An asymmetric nitro-Mannich reaction applicable to alkyl, aryl, and heterocyclic imines

被引：76

作者：

Anderson, JC ^{[1
]}

Howell, GP

Lawrence, RM

Wilson, CS

机构：

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

[2] GlaxoSmithKline Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 14期

关键词：

D O I：

10.1021/jo050762i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A protocol for the enantioselective nitro-Mannich coupling between alkyl, aryl, and heterocyclic p-methoxybenzylimines and trimethylsilylnitropropanate catalyzed by a chiral Bu-t-BOX Cu(II) catalyst is described. It uses the lowest reported loading of commercially available metal catalyst and chiral ligand, and gives the highest yields and selectivities for a broad substrate range including nonaromatic aldimines. The resultant beta-nitroamines are obtained in 70-94% enantiomeric excess in good yield and can be readily reduced to synthetically useful 1,2-diamines.

引用

页码：5665 / 5670

页数：6

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