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

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, Email:

S. Minakata, Y. Morino, Y. Oderaotoshi, M. Komatsu, Org. Lett., 2006, 8, 3335-3337.

DOI: 10.1021/ol061182q


tert-Butyl hypoiodite is a mild and powerful reagent for the cyclization of N-alkenylamides leading to various N-heterocycles. N-alkenylsulfonamides gave three- to six-membered saturated N-heterocycles in good yields, whereas alkenylbenzamide derivatives afforded N-, O- or N-, S-heterocycles.

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Key Words

N-Heterocycles, Aziridines, Azetidines, Piperidines, 2-Oxazolines

ID: J54-Y2006-2170