Litcius/Paper detail

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

Nicholas J. Venditto, Jeffrey A. Boerth

2023Organic Letters19 citationsDOI

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.

Topics & Concepts

ElectrophileChemistryPolarCombinatorial chemistryCatalysisPhotoredox catalysisButyric acidStereocenterOrganic chemistryEnantioselective synthesisPhotocatalysisAstronomyPhysicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods