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Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

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Author(s)

Ryan W. F. Kerr, Mark D. Greenhalgh, Alexandra M. Z. Slawin, Polly L. Arnold, Andrew David Smith

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Abstract

An enantioselective N-heterocyclic carbene catalysed formal [3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the 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 a model to explain these observations.
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Original languageEnglish
Pages (from-to)125-134
JournalTetrahedron: Asymmetry
Volume28
Issue number1
Early online date21 Nov 2016
DOIs
Publication statusPublished - 15 Jan 2017

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