title: Asymmetric synthesis of (alphaR)-polyfluoroalkylated prolinols based on the perfluoroalkyl-induced highly stereoselective reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones.
abstract: Reduction of the obtained chiral (S)- tert-butyl 2-(perfluoroalkanoyl)pyrrolidine-1-carboxylate with sodium borohydride or lithium aluminum hydride proceeded smoothly to give the corresponding (S)- tert-butyl 2-((R)-perfluoro-1-hydroxyalkyl)pyrrolidine-1-carboxylate in yields of 73-97% with excellent diastereoselectivities (up to >98% de), compared with the reduction of nonfluorinated (S)-tert-butyl 2-pentanoylpyrrolidine-1-carboxylate.
authors.affiliation: Department of Materials Science and Technology and Department of Chemistry, Faculty of Engineering, Gifu University, Gifu, Japan. funabiki@gifu-u.ac.jp
authors.forename: Kazumasa
authors.initials: K
authors.lastname: Funabiki
authors.forename: Akitsugu
authors.initials: A
authors.lastname: Shibata
authors.forename: Hiroki
authors.initials: H
authors.lastname: Iwata
authors.forename: Keisuke
authors.initials: K
authors.lastname: Hatano
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Kubota
authors.forename: Kenichi
authors.initials: K
authors.lastname: Komura
authors.forename: Masahiro
authors.initials: M
authors.lastname: Ebihara
authors.forename: Masaki
authors.initials: M
authors.lastname: Matsui