Photoredox-Catalyzed Multicomponent Synthesis of Functionalized γ-Amino Butyric Acids via Reductive Radical Polar Crossover

Abstract

Multicomponent radical polar crossover (RPC) reactions are useful for leveraging both radical and polar bond-forming steps to rapidly build molecular complexity in a single transformation. However, multicomponent RPC reactions that utilize carbonyl π-bond electrophiles are underrepresented in the literature. Herein, we describe a mild, photoredox-catalyzed decarboxylative multicomponent RPC reaction that couples carboxylic acids, Michael acceptors, and carbonyl electrophiles for the formation of diversely functionalized γ-amino butyric acid derivatives. This transformation also facilitates the synthesis of complex and biologically relevant γ-lactam compounds.

Carbamoylarylation of Alkenes with N-Aryl Oxamic Acids Involving 1,4-Aryl Migration Via C(aryl)–N Bond Cleavage

“…This result indicates that the 1,4-aryl migration step is not inhibited by D 2 O in our reaction system. The reported radical-polar crossover reactions of α-aminoalkyl radical, acrylates, and aldehydes demonstrated that the generated enolates reacted with aldehydes to afford the corresponding alcohols . Therefore, the intramolecular trapping of the carbanion was investigated by using alkene 1z possessing the formyl group at the appropriate position (Scheme b).…”