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.
Date made available10 Oct 2016
PublisherUniversity of St Andrews

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