Bifunctional cinchona alkaloid-squaramide-catalyzed highly enantioselective aza-Michael addition of indolines to α,β-unsaturated ketones

An enantioselective aza-Michael addition of indolines to α,β-unsaturated ketones was achieved using a bifunctional cinchona alkaloid-derived chiral squaramide derivative. Various β-indolinyl ketone derivatives were obtained in good to excellent yields and with high enantioselectivity. DDQ or MnO2 oxidation of indoline derivatives provided convenient access to various enantioenriched N-substituted indole derivatives.