Epoxyisoindoline scaffolds can be efficiently assembled through a tandem Ugi-Smiles intramolecular Diels-Alder (US-IMDA) process. Two separable diastereomeric products are obtained through the one-pot multicomponent reaction. Studies have been directed at examination of epimerization conditions for the diastereomers and expanding the scope of this reaction with a range of substituted phenol and isocyanide components. Bromo-substituted 2-nitrophenol has provided significant improvements in reaction yields (80-96%) over non-halogenated analogs. Recent efforts are focused on the use of thiophene-derived components.

Incorporation of heterocyclic aldehydes in Ugi-Smiles Diels-Alder reactions

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.