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An organocatalytic tandem conjugate addition / intramolecular cyclization of malononitrile and conformationally restricted 1,4-dien-3-ones has been developed. A series of cinchona alkaloids and their derivatives were examined as the catalysts. Quinine was found to be the most efficient catalyst in the absence of any additive. The reaction gave 2-amino-4H-pyrans with high yield and excellent enantiopurity using only 5 mol% quinine as the catalyst.

Quinine-catalyzed enantioselective tandem conjugate addition/intramolecular cyclization of malononitrile and 1,4-dien-3-ones