Coupling of α-bromoamides and unactivated alkenes to form γ-lactams through EDA and photocatalysis.

ABSTRACT: γ-Lactams are prevalent in small-molecule pharmaceuticals and provide useful precursors to highly substituted pyrrolidines. Despite numerous methods for the synthesis of this valuable motif, previous redox approaches to γ-lactam synthesis from α-haloamides and olefins require additional electron withdrawing functionality as well as N-aryl substitution to promote electrophilicity of the intermediate radical and prevent competitive O-nucleophilicity about the amide. Using α-bromo imides and α-olefins, our strategy enables the synthesis of monosubstituted protected γ-lactams in a formal [3 + 2] fashion. These species are poised for further derivatization into more complex heterocyclic scaffolds, complementing existing methods. C-Br bond scission occurs through two complementary approac

SUBMITTER: Treacy SM 

PROVIDER: S-EPMC9906710 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature