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Synlett 1991; 1991(7): 511-512
DOI: 10.1055/s-1991-20782
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Optically Active Cyclobutanones from Glycals: Preparation and Regioselective Cleavage

Issam Hanna* , Jingwen Pan, Jean-Yves Lallemand
  • *Laboratoire de Synthèse Organique, École Polytechnique, F-91128 Palaiseau Cedex, France
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Publication Date:
07 March 2002 (online)

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Chiral cyclobutanone-annulated tetrahydropyrans [(2S,5S)-5-benzyloxy/methoxymethoxy-3-(tert-butyldimethylsiloxy-methyl)-2-oxabicyclo[4.2.0]octan-7-ones] were prepared by cycloaddition of 1,1-dichloroketene and glycals followed by dehalogenation. Regioselective cleavage of the cyclobutanone ring has been achieved via the corresponding lactone, enaminoketone or silyl enol ether affording anomeric alkylation and vicinal bifunctionalization of starting glycals.