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
收藏
页码：8120 / 8121
页数：2
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