Organocatalytic enantioselective conjugate addition to alkynones

被引:137
作者
Bella, M [1 ]
Jorgensen, KA [1 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
关键词
D O I
10.1021/ja0493594
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first catalytic enantioselective addition of β-dicarbonyl compounds to alkynones is presented. The conjugate addition proceeds in very high yields, giving a mixture of (Z)- and (E)-enones with up to 95% ee using the cinchona alkaloid [DHQ]2PHAL (5 mol %) as the catalyst. This organocatalytic enantioselective reaction has been further developed to a one-pot procedure to give the optically active (E)-enone adduct using first [DHQ]2PHAL (5 mol %), followed by Bu3P (10 mol %), as the catalysts. Copyright © 2003 American Chemical Society.
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页码:5672 / 5673
页数:2
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