Highly Enantioselective Conjugate Addition of Malononitrile to 2-Enoylpyridines with Bifunctional Organocatalyst

An efficient enantioselective conjugate addition of malononitrile to a range of beta-substituted 2-enoylpyridines catalyzed by cinchona alkaloid-based bifunctional urea catalysts has been developed. Both enantiomers of the products could be achieved with the same level of enantioselectivity by using pseudoenantiomeric catalysts in up to 97% ee and in excellent yields. One of the enantioenriched products has been transformed to a highly functionalized piperidone derivative.