Synthesis of alkyl and aryl C-pyranosides using organozinc reagents via a Ferrier-type rearrangement

The reaction of 1,2-dihydropyranyl acetates with dimethylzinc, diethylzinc and diphenylzinc in the presence of CF3COOH gave the corresponding alky and aryl C-pyranosides via a Ferrier rearrangement in excellent yields. Use of the organo-zinc species, CF3CO2ZnPh, reacted with high stereoselectivity to give the phenyl C-glycosides. Arylzinc chlorides could also be successfully applied to this reaction in the presence of BF3-OEt2. (C) 2004 Elsevier Ltd. All rights reserved.