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

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

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% yi...

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Veröffentlicht in:Organic letters 2022-04, Vol.24 (12), p.2321-2326
Hauptverfasser: Wang, Pengyang, Cen, Shouyi, Gao, Jun, Shen, Ahui, Zhang, Zhipeng
Format: Artikel
Sprache:eng
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Zusammenfassung: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.).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00479