Min Lu - Chiral Brønsted Acid Catalyzed Enantioselective α-Aminoxylation of Enecarbamates

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  Publication Details (including relevant citation   information):

  Angewandte Chemie International Edition


    Volume 49, Issue 46, pages 8588–8592, November     8, 2010  


    DOI: 10.1002/anie.201002640  


  We have reported a facile, practically appealing, highly   enantioselective Brønsted acid-catalyzed

  a-aminoxylation of enecarbamates. This procedure considerably   extend the substrate scope for the a-aminoxylation reaction to   linear and aromatic ketones, allowing convergent and   stereoselective access to valuable a-hydroxy ketones, b-amino   alcohols, and cis-oxazolidinones in their enantiopure form. This   discovery also provides mechanistic insights into the N/O   selectivity of a-aminoxylation.

  Address (URL): http://dx.doi.org/10.1002/anie.201002640