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Paper | Special issue | Vol 88, No. 1, 2014, pp.331-346
Published online, 16th July, 2013
DOI: 10.3987/COM-13-S(S)27
Diastereoselective Synthesis of 3-Fluoro-2-substituted Piperidines and Pyrrolidines

Paul N. Gichuhi, Masami Kuriyama, and Osamu Onomura*

*Department of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

A facile procedure for synthesis of trans-3-fluoro-2-substituted piperidines by utilizing electrophilic fluorination of cyclic enamines and Lewis acid mediated nucleophilic substitution has been developed. Also, optically active trans-2-allyl-3-fluorinated pyrrolidines have been prepared by utilizing nucleophilic fluorination of hydroxyl group of trans-hydroxy-L-proline and Lewis acid mediated diastereoselective allylation as key steps.