Atroposelective Synthesis of Axially Chiral Naphthylpyrroles by a Catalytic Asymmetric 1,3-Dipolar Cycloaddition/Aromatization Sequence
Ian Maclean, Enrique Gallent, Oscar Orozco, Alba Molina, Nuria Rodríguez, Javier Adrio, Juan C. Carretero
Abstract
High Resolution Image Download MS PowerPoint Slide 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.
Topics & Concepts
PyrrolidineEnantioselective synthesisAzomethine ylideAromatizationChemistryCycloadditionCatalysisAxial chirality1,3-Dipolar cycloadditionPyrroleCombinatorial chemistryAlkylationStereochemistryOrganic chemistryAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySynthesis and Properties of Aromatic Compounds