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Synlett 1997; 1997(1): 66-68
DOI: 10.1055/s-1997-705
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Stereoselective Methodology for 1-Aryl-1-alkyl Epoxides via Chromium Tricarbonyl Complexes

S. G. Davies1 , T. Loveridge1 , J. M. Clough2
  • 1Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford OX1 3QY, UK
  • 2ZENECA Agrochemicals, Jealott’s Hill Research Station, Bracknell, Berkshire RG42 6ET, UK
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Publication Date:
22 March 2004 (online)

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Treatment of (1RS,SSR)-(1-phenylsulfinyl-2-valeryl benzene) chromium tricarbonyl 2 with a sulfur ylide results in a highly diastereoselective epoxide formation (d.s.>96:4). Regioselective opening of the epoxide, employing an in situ trapping protocol, allows the synthesis of a highly functionalised, diastereomerically pure benzylic alcohol.

chromium tricarbonyl - stereoselective - epoxide formation

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