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Synlett 1993; 1993(9): 675-676
DOI: 10.1055/s-1993-22568
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Ring-Opening of N-Tosyl Aziridines by Sulphur-Stabilized Nucleophiles

Helen M. I. Osborn* , J. B. Sweeney, Bill Howson
  • *School of Chemistry, University of Bristol, Cantocks Close, Bristol BS8 1TS, England
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Publication Date:
19 March 2002 (online)

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The novel ring-opening reaction of enantiopure N-activated aziridines 1 with anions 2 derived from 1,3-dithiane proceeds regiospecifically at the carbon of lesser substitution. The ring-opened products 3 may efficiently be converted to homochiral 2-tosylaminocarbonyl compounds 4.

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