Enantioselective NHC-catalyzed redox formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

An enantioselective N-heterocyclic carbene (NHC)-catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under NHC-redox catalysis provides the formal cycloaddition products with excellent control of diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of model to explain these observations.