Expanding the Chemical Space of Electrophilic β-Glycosyl β-Lactams through Photoinduced Diastereoselective Functionalization.

Herein, we present a photoinduced diastereoselective C-3 functionalization of electrophilic β-glycosyl β-lactams. The developed protocol is simple, mild, and scalable and explores the use of 3-exomethylene β-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 β-lactam radical intermediate enables the synthesis of various N -phenyl β-glycosyl β-lactams.