Concise syntheses of nonracemic gamma-fluoroalkylated allylic alcohols and amines via an enantiospecific palladium-catalyzed allylic substitution reaction.
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.
Konno
Tsutomu
T
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Sakyo-ku, Matsugasaki, Kyoto 606-8585, Japan. konno@chem.kit.ac.jp
Nagata
Kensuke
K
Ishihara
Takashi
T
Yamanaka
Hiroki
H