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Letter

Practical and Convenient Synthesis of N-Heterocycles: Stereoselective Cyclization of N-Alkenylamides with t-BuOI under Neutral Conditions

Supporting Info

Satoshi Minakata,* Yoshinobu Morino, Yoji Oderaotoshi, and Mitsuo Komatsu*

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan

Org. Lett., 2006, 8 (15), pp 3335–3337

DOI: 10.1021/ol061182q

Publication Date (Web): June 22, 2006

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

, minakata@chem.eng.osaka-u.ac.jp

Abstract

tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cyclization of N-alkenylamides leading to a variety of N-heterocycles under extremely mild conditions. When N-alkenylsulfonamides were employed in the reaction, three- to six-membered saturated N-heterocycles were obtained in good to excellent yields with complete stereoselectivity. The method was applicable to the cyclization of alkenylbenzamide derivatives to afford N-, O- or N-, S-heterocycles.

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