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

Autor: Maclean I; Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain., Gallent E; Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain., Orozco O; Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain., Molina A; Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain., Rodríguez N; Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain.; Institute for Advanced Research in Chemical Sciences (IAdChem) and Center for Innovation in Advanced Chemistry (ORFEO-CINQA), Universidad Autónoma de Madrid, 28049 Madrid, Spain., Adrio J; Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain.; Institute for Advanced Research in Chemical Sciences (IAdChem) and Center for Innovation in Advanced Chemistry (ORFEO-CINQA), Universidad Autónoma de Madrid, 28049 Madrid, Spain., Carretero JC; Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain.; Institute for Advanced Research in Chemical Sciences (IAdChem) and Center for Innovation in Advanced Chemistry (ORFEO-CINQA), Universidad Autónoma de Madrid, 28049 Madrid, Spain.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Feb 02; Vol. 26 (4), pp. 922-927. Date of Electronic Publication: 2024 Jan 24.
DOI: 10.1021/acs.orglett.3c04261
Abstrakt: 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.
Databáze: MEDLINE
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