Catalytic asymmetric Mannich reaction of glycine Schiff bases with α-amido sulfones as precursors of aliphatic imines

被引：31

作者：

Hernando, Elier ^{[1
]}

Gomez Arrayas, Ramon ^{[1
]}

Carretero, Juan C. ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 77期

关键词：

ALPHA; BETA-DIAMINO ACID-DERIVATIVES; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL SIGNIFICANCE; AMINOMETHYLATION; ESTERS; ALDIMINES; TARTRATE; COMPLEX; KETONES; YLIDES;

D O I：

10.1039/c2cc35160a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and practical Cu-I-Fesulphos-catalyzed Mannich reaction of glycinate Schiff bases with aliphatic imines generated in situ from alpha-amido sulfones is described. Imines with linear and branched alkyl chains, including substrates bearing functional groups, can be efficiently applied. The resulting syn-configured orthogonally protected beta-alkyl-alpha,beta-diamino acid derivatives are produced with excellent levels of diastereo-(typically syn/anti > 90 : < 10) and enantioselectivity (generally >= 90% ee).

引用

页码：9622 / 9624

页数：3

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