Base-promoted cascade β-F-elimination/electrocyclization/Diels-Alder/retro-Diels-Alder reaction: efficient access to δ-carboline derivatives.

ABSTRACT: A serendipitous and highly efficient approach for the construction of a variety of δ-carboline derivatives was developed through base-promoted cascade β-F-elimination/electrocyclization/Diels-Alder/retro-Diels-Alder reaction of N-2,2,2-trifluoroethylisatin ketoimine esters with alkynes in good to high yields with excellent regio-/chemoselectivity control. Moreover, a reasonable reaction pathway was proposed, which was in accordance with the prepared reaction intermediate and control experiment results. The δ-carboline product could be easily converted into a new chiral Py-box-type ligand through simple synthetic transformations. This salient strategy featured the advantages of metal-free conditions, excellent regio-/chemoselectivity, good to high yields, and outstanding substrate to

SUBMITTER: Sun XS 

PROVIDER: S-EPMC9473522 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature