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