Titanium-promoted highly stereoselective synthesis of α,α-difluoro-β,γ-dihydroxyester. Simple route to 2-deoxy-2,2-difluororibose

Article abstract of DOI:10.1016/S0022-1139(00)82832-8

The highly stereoselective synthesis of α,α-difluoro-β,γ-dihydroxyesters is described.Reformatsky reaction of bromo- or iododifluoroacetate with D-glyceraldehyde provide (3R,4R)-2,2-difluoro-4,5-O-cyclohexylidene-3-triethylsiloxypentanoic acid ethyl ester in high yield, with more than 95percent diastereoselectivity, by asymmetric induction promoted by Cp2TiCl2.The reaction affords a simple and practical route to 2-deoxy-2,2-difluororibose.