Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of α-substituted α-cyanoacetates and β-dicarbonyl compounds

被引：272

作者：

Saaby, S ^{[1
]}

Bella, M ^{[1
]}

Jorgensen, KA ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 26期

关键词：

D O I：

10.1021/ja047704j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first organocatalytic highly enantioselective reactions of substituted α-cyanoacetates and β-dicarbonyl compounds with azodicarboxylates are reported. In the presence of 0.1-5 mol % of a quinidine-derived alkaloid β-ICD, optically active quaternary hydrazine adducts are obtained in very high yields and with enantioselectivities up to >98% ee. A two-step procedure for the cleavage of the hydrazine N-N bond using SmI2 is also demonstrated. Copyright © 2004 American Chemical Society.

引用

页码：8120 / 8121

页数：2

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