Concise syntheses of nonracemic gamma-fluoroalkylated allylic alcohols and amines via an enantiospecific palladium-catalyzed allylic substitution reaction

Tsutomu Konno; Kensuke Nagata; Takashi Ishihara; Hiroki Yamanaka

doi:10.1021/jo011013d

Concise syntheses of nonracemic gamma-fluoroalkylated allylic alcohols and amines via an enantiospecific palladium-catalyzed allylic substitution reaction

J Org Chem. 2002 Mar 22;67(6):1768-75. doi: 10.1021/jo011013d.

Authors

Tsutomu Konno¹, Kensuke Nagata, Takashi Ishihara, Hiroki Yamanaka

Affiliation

¹ Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Sakyo-ku, Matsugasaki, Kyoto 606-8585, Japan. konno@chem.kit.ac.jp

PMID: 11895391
DOI: 10.1021/jo011013d

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.