Asymmetric Michael addition of arylthiols to α,β-unsaturated carbonyl compounds catalyzed by bifunctional organocatalysts

被引：339

作者：

Li, BJ

Jiang, L

Liu, M

Chen, YC ^{[1
]}

Ding, LS

Wu, Y

机构：

[1] Sichuan Univ, W China Sch Pharm, Dept Med Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

来源：

SYNLETT | 2005年 / 04期

关键词：

bifunctional organocatalyst; thiourea; hydrogen bonding; asymmetric Michael addition; asymmetric protonation;

D O I：

10.1055/s-2005-863710

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bifunctional chiral organocatalysts comprising thiourea and tertiary amine groups were synthesized. They act as efficient catalysts for asymmetric Michael addition of arylthiols to alpha,beta-unsaturated carbonyl compounds. Enantioselectivity up to 85% has been achieved. Asymmetric alpha-protonation reaction (up to 60% ee) can be obtained in the presence of the bifunctional catalyst.

引用

页码：603 / 606

页数：4

共 47 条

[1]

ACHIRAL FC, 2004, SYNLETT, P2374

[2] Organocatalytic asymmetric hydroxylation of β-keto esters:: Metal-free synthesis of optically active anti-diols [J].