Tetrahedron

Electrophilic cyclization of N-alkenylamides using a chloramine-T/I 2 system

…, I Hidaka, Y Oderaotoshi, M Komatsu, S Minakata

Index: Morino, Yoshinobu; Hidaka, Ikumasa; Oderaotoshi, Yoji; Komatsu, Mitsuo; Minakata, Satoshi Tetrahedron, 2006 , vol. 62, # 52 p. 12247 - 12251

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Citation Number: 20

Abstract

A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three-to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the ...

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