Organocatalytic enantioselective nucleophilic vinylic substitution

被引:100
作者
Poulsen, Thomas B. [1 ]
Bernardi, Luca [1 ]
Bell, Mark [1 ]
Jorgensen, Karl Anker [1 ]
机构
[1] Aarhus Univ, Dept Chem, Ctr Catalysis, Danish Natl Res Fdn, DK-8000 Aarhus C, Denmark
关键词
addition-elimination; asymmetric synthesis; organocatalysis; phase-transfer catalysis; vinylation;
D O I
10.1002/anie.200602275
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The clash of hybridizations: A tailored phase-transfer organocatalyst merges sp3-and sp2- hybridized carbon atoms by catalyzing the first enantioselective vinylic substitution (see scheme; EWG = electron-withdrawing group). The method provides access to optically active compounds possessing vinyl-substituted quaternary stereocenters with control of the alkene configuration. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6551 / 6554
页数:4
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