title: Concise syntheses of nonracemic gamma-fluoroalkylated allylic alcohols and amines via an enantiospecific palladium-catalyzed allylic substitution reaction.
abstract: Alpha-fluoroalkylated allyl mesylates reacted with various carboxylates and amines in the presence of tetrakis(triphenylphosphine)palladium(0) catalyst to give the corresponding gamma-fluoroalkylated (E)-allylic alcohol derivatives and amines, respectively, in excellent yields. In almost all cases, no other regio- and stereoisomers were produced. Application of this palladium-catalyzed allylic substitution reaction to various nonracemic mesylates afforded chiral gamma-fluoroalkylated allylic alcohol derivatives and amines without any loss of enantiomeric excess through the reaction.
authors.affiliation: Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Sakyo-ku, Matsugasaki, Kyoto 606-8585, Japan. konno@chem.kit.ac.jp
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Konno
authors.forename: Kensuke
authors.initials: K
authors.lastname: Nagata
authors.forename: Takashi
authors.initials: T
authors.lastname: Ishihara
authors.forename: Hiroki
authors.initials: H
authors.lastname: Yamanaka