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Synlett 1991; 1991(7): 511-512
DOI: 10.1055/s-1991-20782
DOI: 10.1055/s-1991-20782
letter
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Optically Active Cyclobutanones from Glycals: Preparation and Regioselective Cleavage
Further Information
Publication History
Publication Date:
07 March 2002 (online)
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.