Unknown

Dataset Information

0

Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.


ABSTRACT: An intramolecular Ir(III)-catalyzed regiodivergent oxyamination of unactivated alkenes provides valuable ?-lactams, ?-lactones and ?-lactams. The regioselectivity is controlled by the electronically tunable cyclopentadienyl Ir(III)-complexes enabling oxyamination via either 5-exo or 6-endo pathways. With respect to the mechanism, we propose a highly reactive [3.1.0] bicycle intermediate derived from Ir(V) nitrene-mediated aziridination to be a key intermediate toward the synthesis of ?-lactams.

SUBMITTER: Lei H 

PROVIDER: S-EPMC6980349 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

altmetric image

Publications

Ligand Controlled Ir-Catalyzed Regiodivergent Oxyamination of Unactivated Alkenes.

Lei Honghui H   Conway John H JH   Cook Caleb C CC   Rovis Tomislav T  

Journal of the American Chemical Society 20190716 30


An intramolecular Ir(III)-catalyzed regiodivergent oxyamination of unactivated alkenes provides valuable γ-lactams, γ-lactones and δ-lactams. The regioselectivity is controlled by the electronically tunable cyclopentadienyl Ir(III)-complexes enabling oxyamination via either 5-exo or 6-endo pathways. With respect to the mechanism, we propose a highly reactive [3.1.0] bicycle intermediate derived from Ir(V) nitrene-mediated aziridination to be a key intermediate toward the synthesis of γ-lactams. ...[more]

Similar Datasets

| S-EPMC7069249 | biostudies-literature
| S-EPMC6663592 | biostudies-literature
| S-EPMC3419474 | biostudies-literature
| S-EPMC5707484 | biostudies-other
| S-EPMC4097818 | biostudies-literature
| S-EPMC5778876 | biostudies-literature
| S-EPMC6583794 | biostudies-literature
| S-EPMC8157611 | biostudies-literature
| S-EPMC7066668 | biostudies-literature