A tandem Ugi-Smiles Diels-Alder (US-IMDA) process generates epoxyisoindoline scaffolds through an efficient one-pot process. In this stereoselective process, four stereocenters and six new bonds are generated in one synthetic step from achiral starting materials, preparing two separable diastereomeric products. To expand the utility of this reaction, <i>N</i>-heterocyclic phenols and 5-substituted 2-furaldehydes have been explored as reaction components. A small library of epoxyisoindolines have been prepared and derivatized through chemoselective reduction of the nitro substituent. Studies have been directed at optimization of the reaction, purification efforts, and reaction monitoring to provide insight into the mechanistic pathway.

Use of <i>N</i>-heterocyclic phenols as components in Ugi-Smiles Diels-Alder reactions

255th National Meeting (2018)

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Use of N-heterocyclic phenols as components in Ugi-Smiles Diels-Alder reactions