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.

Amino acids U 0400Asymmetric Synthesis of (αR)-Polyfluoroalkylated Prolinols Based on the Perfluoroalkyl-Induced Highly Stereoselective Reduction of Perfluoroalkyl N-Boc-pyrrolidyl Ketones. -Treatment of fluoroalkylated pyrrolidyl ketones like (III) and (V) with NaBH4 allows efficient and highly stereoselective access to fluoroalkylated prolinols. In contrast, reduction of the nonfluorinated analogue (VII) proceeds only with low to moderate stereoselectivity. -(FUNABIKI*, K.; SHIBATA, A.; IWATA, H.; HATANO, K.; KUBOTA, Y.; KOMURA, K.; EBIHARA, M.; MATSUI, M.; J. Org. Chem. 73 (2008) 12, 4694-4697; Dep. Mater. Sci. Technol., Fac. Eng., Gifu Univ., Yanagido, Gifu 501-11, Japan; Eng.) -Jannicke 42-191

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Transesterification O 0315Synthesis of Secondary α-Perfluoroalkyland Tertiary α,α-Bis(perfluoroalkyl)-N-methylprolinols and Their Catalytic Activities in the Acyl Transfer Reaction. -(FUNABIKI*, K.; SHIBATA, A.; HATANO, K.; MATSUI, M.; J. Fluorine Chem. 130 (2009) 4, 444-448; Dep. Mater. Sci. Technol., Fac. Eng., Gifu Univ.,