Organocatalytic asymmetric Michael reaction of cyclic 1,3-dicarbonyl compounds and α,β-unsaturated ketones -: A highly atom-economic catalytic one-step formation of optically active warfarin anticoagulant

被引：243

作者：

Halland, N ^{[1
]}

Hansen, T ^{[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 | 2003年 / 42卷 / 40期

关键词：

asymmetric catalysis; enones; Michael addition; natural products; synthetic methods;

D O I：

10.1002/anie.200352136

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A broad range of Michael adducts 3 were obtained by the organocatalytic asymmetric Michael addition of cyclic 1,3-dicarbonyl compounds 1 to α,β-unsaturated ketones 2. The reaction allows a one-step synthesis of the optically active anti-coagulant warfarin and several analogues 3 on a kilogram scale in up to 99% yield with 88% ee (>99.9% ee after a single recrystallization).

引用

页码：4955 / 4957

页数：3

共 26 条

[1]

[Anonymous], [No title captured], Patent No. 0043003

[2]

[Anonymous], COMPREHENSIVE ASYMME

[3] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].