Asymmetric Synthesis of (α<i>R</i>)-Polyfluoroalkylated Prolinols Based on the Perfluoroalkyl-Induced Highly Stereoselective Reduction of Perfluoroalkyl <i>N</i>-Boc-pyrrolidyl Ketones

Reduction of the obtained chiral (<i>S</i>)-<i>tert</i>-butyl 2-(perfluoroalkanoyl)pyrrolidine-1-carboxylate with sodium borohydride or lithium aluminum hydride proceeded smoothly to give the corresponding (<i>S</i>)-<i>tert</i>-butyl 2-((<i>R</i>)-perfluoro-1-hydroxyalkyl)pyrrolidine-1-carboxylate in yields of 73−97% with excellent diastereoselectivities (up to >98% de), compared with the reduction of nonfluorinated (<i>S</i>)-<i>tert</i>-butyl 2-pentanoylpyrrolidine-1-carboxylate.