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Synlett 1996; 1996(4): 401-403
DOI: 10.1055/s-1996-5418
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Chiral Auxiliaries in the Vinyl Epoxide - Dihydrofuran Rearrangement

Andrei S. Batsanov, Andrew L. J. Byerley, Judith A. K. Howard, Patrick G. Steel*
  • *Department of Chemistry, Science Laboratories, University of Durham, South Road, Durham DH1 3LE, email p.g.steel@durham.ac.uk
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Publication Date:
31 December 2000 (online)

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Reasonable asymmetric induction can be obtained in the vinyl epoxide-dihydrofuran rearrangement through the use of established chiral auxiliaries. The diastereomeric products are readily separated to provide access to enantiomerically pure tetrahydrofuran derivatives.

vinyl epoxide-dihydrofuran rearrangement - chiral auxiliary - oxazolidinone - phenylmenthol