Synlett 1997; 1997(8): 1001-1003
DOI: 10.1055/s-1997-949
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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: [email protected]
  • 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.
Further Information

Publication History

Publication Date:
31 December 2000 (online)

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.