Photoredox-enabled 1,2-dialkylation of α-substituted acrylates <i>via</i> Ireland–Claisen rearrangement
Roman Kleinmans, Leon E. Will, J. Luca Schwarz, Frank Glorius
Abstract
) bonds, thus providing rapid access to complex tertiary carboxylic acids in a single step. Moreover, this strategy enables the efficient synthesis of highly attractive α,α-dialkylated γ-amino butyric acids (GABAs) when α-silyl amines are used as radical precursors - a structural motif that was still inaccessible in related transformations. Depending on the nature of the radical precursors and their inherent oxidation potentials, either a photoredox-induced radical chain or a solely photoredox mechanism is proposed to be operative.
Topics & Concepts
Claisen rearrangementChemistryCarroll rearrangementCascadePhotocatalysisStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryCatalysisChromatographyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods