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Amine-Promoted, Organocatalytic Aziridination of Enones

Alan Armstrong,* Carl A. Baxter, Scott G. Lamont, Andrew R. Pape and Richard Wincewicz

*Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, United Kingdom, Email:

A. Armstrong, C. A. Baxter, S. G. Lamont, A. R. Pape, R. Wincewicz, Org. Lett., 2007, 9, 351-353.

DOI: 10.1021/ol062852v

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N-N ylides for the aziridination of a range of enone systems can be prepared by in situ amination of a tertiary amine. The amine may be used sub-stoichiometrically, and promising levels of enantioselectivity are observed with quinine as promoter.

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proposed mechanism

Key Words

Aziridines, Organocatalysis

ID: J54-Y2007-0230