Asymmetric synthesis of (alphaR)-polyfluoroalkylated prolinols based on the perfluoroalkyl-induced highly stereoselective reduction of perfluoroalkyl N-Boc-pyrrolidyl ketones.
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.
Funabiki
Kazumasa
K
Department of Materials Science and Technology and Department of Chemistry, Faculty of Engineering, Gifu University, Gifu, Japan. funabiki@gifu-u.ac.jp
Shibata
Akitsugu
A
Iwata
Hiroki
H
Hatano
Keisuke
K
Kubota
Yasuhiro
Y
Komura
Kenichi
K
Ebihara
Masahiro
M
Matsui
Masaki
M