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Letter

Cp*Ir Complex-Catalyzed N-Heterocyclization of Primary Amines with Diols: A New Catalytic System for Environmentally Benign Synthesis of Cyclic Amines

Supporting Info

Ken-ichi Fujita,* Takeshi Fujii, and Ryohei Yamaguchi*

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

Org. Lett., 2004, 6 (20), pp 3525–3528

DOI: 10.1021/ol048619j

Publication Date (Web): September 9, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, fujitak@kagaku.mbox.media.kyoto-u.ac.jp

Abstract

A new efficient method for the N-heterocyclization of primary amines with diols catalyzed by a Cp*Ir complex was developed. A variety of five-, six-, and seven-membered cyclic amines were synthesized in good to excellent yields with the formation of only water as a byproduct. A two-step asymmetric synthesis of (S)-2-phenylpiperidine was also achieved using (R)-1-phenylethylamine as a starting primary amine.

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Published In Issue September 30, 2004
Received July 17, 2004

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Letter

Cp*Ir Complex-Catalyzed N-Heterocyclization of Primary Amines with Diols: A New Catalytic System for Environmentally Benign Synthesis of Cyclic Amines