Organic letters

Practical and convenient synthesis of N-heterocycles: stereoselective cyclization of N-alkenylamides with t-BuOI under neutral conditions

S Minakata, Y Morino, Y Oderaotoshi, M Komatsu

Index: Minakata, Satoshi; Morino, Yoshinobu; Oderaotoshi, Yoji; Komatsu, Mitsuo Organic Letters, 2006 , vol. 8, # 15 p. 3335 - 3337

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Citation Number: 64

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- ...