Incorporating azaheterocycle functionality in intramolecular aerobic, copper-catalyzed aminooxygenation of alkenes.

ABSTRACT: Despite the maturity of alkene 1,2-difunctionalization reactions involving C-N bond formation, a key limitation across aminofunctionalization methods is incompatibility with substrates bearing medicinally relevant N-heterocycles. Using a cooperative ligand-substrate catalyst activation strategy, we have developed an aerobic, copper-catalyzed alkene aminooxygenation method that exhibits broad tolerance for β,γ-unsaturated carbamates bearing aromatic azaheterocycle substitution. The synthetic potential of this methodology was demonstrated by engaging a densely-functionalized vonoprazan analogue and elaborating an amino oxygenated product to synthesize a heteroarylated analogue precursor of the FDA-approved antibiotic chloramphenicol.

SUBMITTER: DeCicco EM 

PROVIDER: S-EPMC11386206 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature