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Synthesis 2008(24): 3903-3918  
DOI: 10.1055/s-0028-1083240
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Concise Route to Difluorinated Analogues of Cyclitols and Sugars

Erwan Kérourédana, Jonathan M. Percy*b, Giuseppe Rinaudob, Kuldip Singha
a Department of Chemistry, University of Leicester, University Road, Leicester LE1 7RE, UK
b WestCHEM Department of Pure and Applied Chemistry, Thomas Graham Building, 295 Cathedral Street, Glasgow G1 1XL, UK
Fax: +44(141)5484822; e-Mail: jonathan.percy@strath.ac.uk;
Further Information

Publication History

Received 5 September 2008
Publication Date:
01 December 2008 (online)

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Abstract

Allyl ethers of trifluoroethanol are transformed to di­fluorinated analogues of deoxysugars via concise sequences involving dehydrofluorination/metallation, [3,3]-Claisen rearrangement, reduction, and RCM, affording cyclohexenediol substrates for dihydroxylation reactions.

Key words

carbasugars - cyclitols - difluorinated - metathesis - dihydroxylation

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