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

ABSTRACT: 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.

SUBMITTER: Tordato EA 

PROVIDER: S-EPMC11232025 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature