@article{oai:niigata-u.repo.nii.ac.jp:00001694, author = {Osawa, Chika and Tateyama, Minami and Miura, Kensuke and Tayama, Eiji and Iwamoto, Hajime and Hasegawa, Eietsu}, issue = {2}, journal = {Heterocycles, Heterocycles}, month = {Dec}, note = {Aza–Prins cyclization reactions of N-tosyl-3-butenylamine with p-methoxybenzaldehyde, 1-naphthaldehyde and 2-naphthaldehyde take place efficiently using a combination of ferric chloride and 1-butyl-3-methylimidazolium hexafluorophosphate in benzotrifluoride (FeIm–BTF procedure). The new methodology, leading to formation of target N-tosyl-4-chloro-2-substituted piperidines, is superior to the one using 1-butyl-3-methylimidazolium tetrachloroferrate. The FeIm–BTF procedure was also applied to aza–Prins cyclization reactions of other aldehydes. Finally, the effects of imidazolium salts on aza–Prins cyclization reaction promoted by boranetrifluoride-diethyl ether complex, leading to formation of fluorinated piperidines, were explored.}, pages = {1211--1226}, title = {AN EFFECTIVE PROCEDURE TO PROMOTE AZA-PRINS CYCLIZATION REACTIONS EMPLOYING A COMBINATION OF FERRIC CHLORIDE AND AN IMIDAZOLIUM SALT IN BENZOTRIFLUORIDE}, volume = {86}, year = {2012} }