Molecular flavin catalysts for C-H functionalisation and derivatisation of dehydroamino acids.

ABSTRACT: In nature, the isoalloxazine heterocycle of flavin cofactors undergoes reversible covalent bond formation with a variety of different reaction partners. These intermediates play a crucial role inter alia as the signalling states and in selective catalysis reactions. In the organic laboratory, covalent adducts with a new carbon-carbon bond have been observed with photochemically excited flavins but have, so far, only been regarded as dead-end side products. We have identified a series of molecular flavins that form adducts resulting in a new C-C bond at the C4a-position through allylic C-H activation and dehydroamino acid oxidation. Typically, these reactions are of radical nature and a stepwise pathway is assumed. We could demonstrate that these adducts are no dead-end and that the

SUBMITTER: Rehpenn A 

PROVIDER: S-EPMC9728571 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature