Multicomponent coupling reactions (MCRs), such as the one-pot Ugi-Smiles reaction, can efficiently provide access to diverse scaffolds. A novel five-component oxy-Michael Ugi-Smiles reaction was observed when a conjugated aldehyde component was used in the presence of alcoholic solvents. This process tolerates a range of substituted alcohols and isocyanides. Current efforts are focused on the optimization of reaction conditions, use of substituted <i>trans</i>-cinnamaldehyde derivatives, and mechanistic studies. Variations in the aldehyde and phenol components modify the reaction efficiency and ease of product isolation. These preliminary studies provide an understanding of the scope of this reaction along with access to a diverse product library.

Exploration of Ugi-Smiles reactions involving oxy-Michael additions

255th National Meeting (2018)

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