Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines

…, EB Hay, SJ Geib, DP Curran

Index: Zhang, Hanmo; Hay, E. Ben; Geib, Steven J.; Curran, Dennis P. Journal of the American Chemical Society, 2013 , vol. 135, # 44 p. 16610 - 16617

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Citation Number: 15

Abstract

Radical cyclizations of cyclic ene sulfonamides provide stable bicyclic and tricyclic aldimines and ketimines in good yields. Depending on the structure of the precursor, the cyclizations occur to provide fused and spirocyclic imines with five-, six-, and seven-membered rings. The initial radical cyclization produces an α-sulfonamidoyl radical that undergoes elimination to form the imine and a phenylsulfonyl radical. In a related method, 3, 4- ...

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