The Ugi-Smiles Diels-Alder (US-IMDA) tandem reaction involves the use of a conjugated, heterocyclic aldehyde component with a phenol, an isocyanide, and an amine to provide access to conformationally-constrained oxatricycles. Alterations to the isocyanide component have led to significant variations in product yields (10-70%). Current efforts are focused on variation of the phenol component through examination of halogen-substituted derivatives to increase product diversity. Use of substituted isocyanide and phenol components have shown that substitution patterns on these components significantly affect the reaction yields and the diastereoselectivity of the US-IMDA process.

Evaluation of phenol modification in tandem Ugi-Smiles Diels-Alder reactions

255th National Meeting (2018)

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