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Synlett 1997; 1997(8): 1001-1003
DOI: 10.1055/s-1997-949
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Stereoselective Synthesis of a Bicyclic Ketooxetane via a Thionium Ion-Mediated Cyclisation Reaction

Donald Craig1 , Ronnie M. Lawrence2 , David J. Tapolczay3
  • 1Department of Chemistry, Imperial College of Science, Technology and Medicin, London SW7 2AY, U.K., Fax: +44 171 594 5804; e-mail: dcraig@ic.ac.uk
  • 2Department of Chemistry, Imperial College of Science, Technology and Medicin, London SW7 2AY, U.K.
  • 3Glaxo Wellcome Research and Development Ltd, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, U.K.
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Publikationsdatum:
31. Dezember 2000 (online)

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The synthesis of a bicyclic ketooxetane using as the key step the ethylaluminium dichloride-mediated cyclisation of a Z-silyl enol ether onto a thionium ion 'trigger' attached to a five-membered carbocyclic template is described. Attempted cyclisation of the analogous substrate possessing a six-membered ring did not afford the oxetane, but instead the product of 1,2-hydride shift. The mechanism of this unexpected transformation was conclusively established by analysis of the products of attempted cyclisation of a deuterium-labeled substrate.

ketooxetane - cyclisation - thionium - stereoselective - hydride shift