A one-pot multicomponent coupling process, combining the Diels-Alder and Ugi-Smiles reactions to synthesize substituted epoxyisoindolines, is reported. Preliminary studies support a reaction pathway that involves imine formation, Diels-Alder cyclization, and a Smiles rearrangement. In this stereoselective tandem process, six new bonds and four stereocenters are generated in one synthetic step from achiral starting materials. Current efforts examine the impact of structural variation of aldehydes, amines, and phenols on access to functionally-diverse epoxyisoindoline products.

Efficient assembly of epoxyisoindoline derivatives through a tandem Diels-Alder Ugi-Smiles process

249th National Meeting (2015)

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