Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to α,β-unsaturated aldehydes

被引：394

作者：

Marigo, M ^{[1
]}

Schulte, T ^{[1
]}

Franzén, J ^{[1
]}

Jorgensen, KA ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 45期

关键词：

D O I：

10.1021/ja055291w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to α,β-unsaturated aldehydes are presented. The development is based, first, on an organocatalyzed highly enantioselective nucleophilic thiol addition to the β-carbon atom in the iminium ion intermediate, followed by an electrophilic amination of the α-carbon atom to the enamine intermediate. The multicomponent reactions proceed to give enantiopure amino-thiols in moderate to good yields. Furthermore, the organocatalyzed thiol addition to α,β-unsaturated aldehydes takes place in good yields and excellent enantioselectivities. Copyright © 2005 American Chemical Society.

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页码：15710 / 15711

页数：2

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