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

Shicheng Shi; Michal Szostak

doi:10.1021/acs.orglett.5b02732

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

Org Lett. 2015 Oct 16;17(20):5144-7. doi: 10.1021/acs.orglett.5b02732. Epub 2015 Oct 6.

Authors

Shicheng Shi¹, Michal Szostak¹

Affiliation

¹ Department of Chemistry, Rutgers University , 73 Warren Street, Newark, New Jersey 07102, United States.

PMID: 26440204
DOI: 10.1021/acs.orglett.5b02732

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't