title: An in situ directing group strategy for chiral anion phase-transfer fluorination of allylic alcohols.
abstract: An enantioselective fluorination of allylic alcohols under chiral anion phase-transfer conditions is reported. The in situ generation of a directing group proved crucial for achieving effective enantiocontrol. In the presence of such a directing group, a range of acyclic substrates underwent fluorination to afford highly enantioenriched α-fluoro homoallylic alcohols. Mechanistic studies suggest that this transformation proceeds through a concerted enantiodetermining transition state involving both C-F bond formation and C-H bond cleavage.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Weiwei
authors.initials: W
authors.lastname: Zi
authors.forename: Yi-Ming
authors.initials: YM
authors.lastname: Wang
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D000838:Anions / Q000737:chemistry; D054879:Halogenation; D008958:Models, Molecular; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000838:Anions; D020005:Propanols; C006463:allyl alcohol