Highly enantioselective direct organocatalytic α-chlorination of ketones

被引：111

作者：

Marigo, M ^{[1
]}

Bachmann, S ^{[1
]}

Halland, N ^{[1
]}

Braunton, A ^{[1
]}

Jorgensen, KA ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 41期

关键词：

asymmetric catalysis; halogenation; homogeneous catalysis; ketones;

D O I：

10.1002/anie.200460462

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A C2-symmetric diamine serves as the organocatalyst in an asymmetric α-chlorination reaction of simple ketones (e.g., cyclohexanone, diethyl ketone). Optically active α-chloroketones are formed with excellent enantioselectivities using N-chlorosuccinimide (NCS) as the chlorine source (see scheme). These products have broad synthetic utility, in particular for pharmaceutical applications.

引用

页码：5507 / 5510

页数：4

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[1]

[Anonymous], 2004, ANGEW CHEM, V116, P1292

[2] Direct catalytic enantioselective α-aminoxylation of ketones:: A stereoselective synthesis of α-hydroxy and α,α′-dihydroxy ketones [J].