title: Stereoselective Reformatskii-Claisen rearrangement: synthesis of 2',3'-dideoxy-6',6'-difluoro-2'-thionucleosides.
abstract: A new approach for the stereoselective synthesis of 2',3'-dideoxy-6',6'-difluoro-2'-thionucleosides, analogues of highly bioactive L-OddC and 3TC, has been developed via TMSCl/pyridine induced stereoselective Reformatskii-Claisen rearrangement of secondary allyl chlorodifluoroacetate and then a regioselective Pummerer reaction to introduce bases.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.
authors.forename: Feng
authors.initials: F
authors.lastname: Zheng
authors.forename: Xingang
authors.initials: X
authors.lastname: Zhang
authors.forename: Feng-Ling
authors.initials: FL
authors.lastname: Qing
mesh_terms: D018360:Crystallography, X-Ray; D005461:Fluorine / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry; D013237:Stereoisomerism; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009705:Nucleosides; D013872:Thionucleosides; D005461:Fluorine