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A concise route to difluorinated analogues of cyclitols and sugars

Kerouredan, E. and Percy, J.M. and Rinaudo, G. and Singh, K. (2008) A concise route to difluorinated analogues of cyclitols and sugars. Synthesis (24). pp. 3903-3918. ISSN 0039-7881

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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.