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Synlett 1995; 1995(4): 339-340
DOI: 10.1055/s-1995-4966
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An Unexpected Rearrangement of the Bicyclo[2.2.1]-hepten System

Christophe Cinquin, Iris Schaper, Gérard Mandville, Robert Bloch*
  • *Laboratoire des Carbocycles, URA CNRS 478, Institut de Chimie Moléculaire d’Orsay, Bât. 420, Université de Paris-Sud, 91405 ORSAY, France
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Publication Date:
31 December 2000 (online)

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The enzyme catalyzed transesterification of vinylacetate with the meso diol 4 gave the enantiopure corresponding monoacetate 3. The triflate generated from this hydroxy acetate lead to a chiral, non racemic substituted furan via a new rearrangement of the bicyclo[2.2.1] skeleton.

Transesterification - Lipase PS - Rearrangement - Chiral furan

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