The Ugi-Smiles reaction is the multicomponent coupling of a phenol, amine, aldehyde, and isocyanide used to generate highly functionalized amides in a single synthetic step. In the presence of a conjugated, heterocyclic aldehyde, a tandem Ugi-Smiles Diels-Alder process occurs. Preliminary studies support a reaction pathway that involves imine formation, Diels-Alder cyclization, and then completion of the Ugi-Smiles reaction. In this stereoselective tandem process, six new bonds and four stereocenters are generated in one synthetic step from achiral starting materials, producing a functionalized epoxyisoindoline skeleton. Current efforts are focused on the use of substituted allylamines and isocyanides to probe the reaction tolerance to component variation.

Amine and isocyanide variation in the Ugi-Smiles Diels-Alder tandem process

249th National Meeting (2015)

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