Oxa-Michael/Ugi-Smiles cascade reaction with α,β-unsaturated aldehydes

[Display omitted] •Oxy-Michael additions to α,β-unsaturated aldehydes.•Observation of a five-component coupling, formally an oxa-Michael/Ugi-Smiles Cascade.•Intermolecular conjugate additions to trans-cinnamaldehyde derivatives. Use of α,β-unsaturated aldehydes as components in Ugi-Smiles couplings of 2-nitrophenol with alkyl isocyanides and primary amines provides ready access to γ-alkoxy substituted amides when performed in the presence of alcoholic solvents. The observed five component coupling forms these adducts via a cascade event involving an oxa-Michael conjugate addition and an Ugi-Smiles multicomponent reaction. Five bonds and two stereocenters are generated in this diastereoselective formation of γ-alkoxy substituted amides in moderate to good yields.