Catalytic asymmetric conjugate addition of isocyanoacetate to ()-3-substituted-2-(4-pyridyl)-acrylonitrile, a reactive class of Michael acceptor

( Z )-3-Substituted-2-(4-pyridyl)-acrylonitriles, a reactive class of Michael acceptors obtained exclusively as a single ( Z ) isomer, reacted with un-substituted isocyanoacetate esters mediated by phase-transfer catalysis to give, after base promoted cyclisation, functionalized imines in up to 94% ee and as a single diastereoisomer. Un-substituted isocyanoacetate ethyl ester reacted with Michael acceptors 1a-m under the catalysis of Cinchona based quaternary ammonium salts providing imines 4a-m as a single diastereoisomer and in up to 94% ees.