Enantioselective oxidative coupling of methyl 3-hydroxy-2-naphthoate using mono-N-alkylated octahydrobinaphthyl-2,2′-diamine ligand

Kyoung Hoon Kim, Dae Woong Lee, You Sang Lee, Dong Hyun Ko, Deok-Chan Ha

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

Mono-N-alkylated octahydrobinaphthyl-2,2′-diamine (H 8-BINAM) chiral ligands were employed in the catalytic and asymmetric oxidative coupling of methyl 3-hydroxy-2-naphthoate to the corresponding binaphthol derivative. The diamine ligand with one N-(3-pentyl) group shows highest enantioselectivity in the biaryl coupling among other BINAM derivatives, and the coupling reaction proceeds faster than the reactions using alkanediamine ligands.

Original languageEnglish
Pages (from-to)9037-9042
Number of pages6
JournalTetrahedron
Volume60
Issue number41
DOIs
Publication statusPublished - 2004 Oct 4

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Keywords

  • Asymmetric
  • Biaryl
  • Binaphthol
  • Catalytic
  • Coupling
  • Oxidation

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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