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
Kazumasa Funabiki
Akitsugu Shibata
Hiroki Iwata
Keisuke Hatano
Yasuhiro Kubota
Kenichi Komura
Masahiro Ebihara
Masaki Matsui
10.1021/jo8004952.s002
https://acs.figshare.com/articles/dataset/Asymmetric_Synthesis_of_i_R_i_Polyfluoroalkylated_Prolinols_Based_on_the_Perfluoroalkyl_Induced_Highly_Stereoselective_Reduction_of_Perfluoroalkyl_i_N_i_Boc_pyrrolidyl_Ketones/2932669
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.
2008-06-20 00:00:00
Perfluoroalkyl N
Asymmetric Synthesis
Stereoselective Reduction
sodium borohydride
lithium aluminum hydride
butyl
tert