Organocatalytic Enantioselective Nucleophilic Vinylic Substitution by α-Substituted-α-Cyanoacetates under Phase-Transfer Conditions
The Journal of Organic Chemistry2007Vol. 72(8), pp. 3053–3056
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Abstract
The organocatalytic enantioselective formation of vinyl-substituted all-carbon quaternary stereocenters via nucleophilic vinylic substitution by alpha-substituted-alpha-cyanoacetates is presented. The reaction proceeds well for different alpha-substituted-alpha-cyanoacetates and beta-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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