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Organocatalytic Enantioselective Nucleophilic Vinylic Substitution by α-Substituted-α-Cyanoacetates under Phase-Transfer Conditions

Mark Bell, Thomas B. Poulsen and Karl Anker Jørgensen*

*Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark, Email: kajchem.au.dk

M. Bell, T. B. Poulsen, K. A. Jørgensen, J. Org. Chem., 2007, 72, 3053-3056.

DOI: 10.1021/jo070024p (free Supporting Information)


Abstract

An organocatalytic highly enantioselective formation of vinyl-substituted all-carbon quaternary stereocenters proceeds in good yield via nucleophilic vinylic substitution of various α-substituted-α-cyanoacetates with α-chloroalkenones using a dimeric cinchona alkaloid phase-transfer catalyst.


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Key Words

Organocatalysis, Active Methylene Compounds, Enones


ID: J42-Y2007-1130