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Paper | Special issue | Vol 74, No. 1, 2007, pp.673-682
Published online, 12th October, 2007
DOI: 10.3987/COM-07-S(W)51
An Efficient Synthesis of Nitrogen Heterocycles by Cp*Ir-Catalyzed N-Cycloalkylation of Primary Amines with Diols

Ken-ichi Fujita, Takeshi Fujii, Atsuo Komatsubara, Youichiro Enoki, and Ryohei Yamaguchi*

*Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan


A new efficient method for the N-cycloalkylation of primary amines with diols catalyzed by a Cp*Ir complex have been developed. A variety of five-, six-, and seven-membered cyclic amines are synthesized in good to excellent yields in environmentally benign and atom economical manner with the formation of only water as a coproduct. A large scale synthesis of N-benzylpiperidine and a two-step asymmetric synthesis of (S)-2-phenylpiperidine using (R)-1-phenylethylamine as a starting primary amine have been also achieved.