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

Abstract

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.

Keywords

• Ugi-Smiles
• Oxa-Michael
• Multicomponent reaction