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Article

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

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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

J. Org. Chem., 2007, 72 (8), pp 3053–3056

DOI: 10.1021/jo070024p

Publication Date (Web): March 20, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kaj@chem.au.dk

Abstract

The organocatalytic enantioselective formation of vinyl-substituted all-carbon quaternary stereocenters via nucleophilic vinylic substitution by α-substituted-α-cyanoacetates is presented. The reaction proceeds well for different α-substituted-α-cyanoacetates and β-chloroalkenones using a dimeric cinchona alkaloid phase-transfer catalyst giving the products in good yield and with enantioselectivities up to 98% ee.

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Published In Issue April 13, 2007
Received January 5, 2007

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Article

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

Abstract

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SciFinder Links

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Recommend & Share

Related Content

Intriguing Behavior of Cinchona Alkaloids in the Enantioselective Organocatalytic Hydroxyamination of α-Substituted-α-cyanoacetates

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