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Synlett 2000; 2000(10): 1408-1410
DOI: 10.1055/s-2000-7638
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The Synthesis of Chiral Polyhydroxylated Pyrrolidines Using a Reverse-Cope Cyclisation

Ian A. O'Neil* , Ed Cleator, Neal Hone, J. Mike Southern, David J. Tapolczay
  • *Department of Chemistry, University of Liverpool, Crown St, Liverpool L69 7ZD, UK; Fax + 44 (0) 151-794-3588; E-mail: ion@liv.ac.uk
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Publication Date:
31 December 2000 (online)

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Ring opening of (2S,3R)-1,2-epoxy-4-penten-3-ol with N-benzylhydroxylamine hydrochloride and NaOMe in methanol gives the amine oxide (9) as a single diastereoisomer in 72% yield. Catalytic hydrogenation furnishes the parent homochiral pyrrolidine (10) in quantitative yield.

pyrrolidines - asymmetric synthesis - cyclisation - hydroxylamine - reverse-Cope