Abstract

Herein, we present a photoinduced diastereoselective C-3 functionalization of electrophilic beta-glycosyl beta-lactams. The developed protocol is simple, mild, and scalable and explores the use of 3-exomethylene beta-lactams as reaction partners in a Giese type reaction. The key nucleophilic alkyl radical is generated by a photoinduced electron transfer process in the EDA complex formed by NHPI and Hantzsch esters. The diastereoselective hydrogen atom transfer to the beta-lactam radical intermediate enables the synthesis of various N-phenyl beta-glycosyl beta-lactams.