Konno Tsutomu, Nagata Kensuke, Ishihara Takashi, Yamanaka Hiroki
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Sakyo-ku, Matsugasaki, Kyoto 606-8585, Japan.
J Org Chem. 2002 Mar 22;67(6):1768-75. doi: 10.1021/jo011013d.
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.
