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Synlett 1991; 1991(6): 403-404
DOI: 10.1055/s-1991-20742
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Regio- and Stereoselective Opening of Phenyloxirane by Lithium Azide: A Direct Access to 2-Azido-1-phenylethanol

Alain Guy* , Thierry Dubuffet, Joël Doussot, Annie Godefroy-Falguieres
  • *Laboratoire de Chimie Organique (URA 1103) Conservatoire National des Arts et Métiers, 292 rue Saint-Martin, F-75141 Paris Cedex 03, France
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Publication Date:
07 March 2002 (online)

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Regio-and stereoselective ring opening of styrene oxide (phenyloxirane) at the non-benzylic position was achieved by lithium azide/hexamethylphosphoric triamide. Optically pure (R)-2-azido-1-phenylethanol was obtained from the readily available (R)-phenyloxirane with complete retention of configuration.

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