Novel Axially Chiral Ligand-Enabled Copper-Catalyzed Asymmetric Oxidative Coupling of 2-Naphthols for the Synthesis of 6,6'-Disubstituted BINOLs.

Journal

Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393

Informations de publication

Date de publication:
01 Apr 2022
Historique:
pubmed: 22 3 2022
medline: 22 3 2022
entrez: 21 3 2022
Statut: ppublish

Résumé

Novel axially chiral ligands have been designed and synthesized by merging the chelating picolinic acid with substituted BINOLs. The in-situ-prepared copper catalysts from the ligands and CuI enable the asymmetric oxidative coupling of 2-naphthols, affording 6,6'-disubstituted BINOLs in up to 89% yield with good enantioselectivities (up to 96:4 e.r.).

Identifiants

DOI: 10.1021/acs.orglett.2c00479 PMID: 35311255
pubmed: 35311255
doi: 10.1021/acs.orglett.2c00479
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

2321-2326

Auteurs

Pengyang Wang (P)

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, China.

Shouyi Cen (S)

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, China.

Jun Gao (J)

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, China.

Ahui Shen (A)

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, China.

Zhipeng Zhang (Z)

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, 130 Meilong Road, Shanghai 200237, China.
ORCID: 0000-0003-2767-0904

Classifications MeSH