Atroposelective Synthesis of Axially Chiral Naphthylpyrroles by a Catalytic Asymmetric 1,3-Dipolar Cycloaddition/Aromatization Sequence.

ABSTRACT: A straightforward methodology for the enantioselective preparation of axially chiral 2-naphthylpyrroles has been developed. This protocol is based on a Cu^I/Fesulphos-catalyzed highly enantioselective 1,3-dipolar cycloaddition of an azomethine ylide followed by pyrrolidine alkylation and pyrrolidine to pyrrole oxidation. The mild conditions employed in the DDQ/blue light-mediated aromatization process facilitate an effective central-to-axial chirality transfer affording the corresponding pyrroles with high atroposelectivity.

SUBMITTER: Maclean I 

PROVIDER: S-EPMC10845160 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature