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Aminoketyl Radicals in Organic Synthesis: Stereoselective Cyclization of Five- and Six-Membered Cyclic Imides to 2‑Azabicycles Using SmI2–H2O

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journal contribution
posted on 2015-10-16, 00:00 authored by Shicheng Shi, Michal Szostak
Synthetic application of aminoketyl radicals [R–C(O)­NR′R″] formed by a direct electron capture into the amide bond is limited. Herein, we demonstrate addition of aminoketyl radicals to unactivated alkenes using SmI2–H2O as a crucial promoter based on the generic five- and six-membered imide template. Notably, this method enables direct access to aminoketyl radicals with wide-ranging applications in synthesis for the formation of C–C bonds adjacent to nitrogen via polarity reversal.