Expanding the Chemical Space of Electrophilic β-Glycosyl β-Lactams through Photoinduced Diastereoselective
Éverton A Tordato1, Renan O Gonçalves1, Lucas L Baldassari1,2
1Laboratory for Sustainable Organic Synthesis and Catalysis - Chemistry Department - Federal University of São Carlos - UFSCar, São Carlos, São Paulo 13565-905, Brazil.
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.
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