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

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...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 41; pp. 9037 - 9042
Main Authors Kim, Kyoung Hoon, Lee, Dae-Woong, Lee, You-Sang, Ko, Dong-Hyun, Ha, Deok-Chan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 04.10.2004
Elsevier
Subjects
Asymmetric
Biaryl
Binaphthol
Catalytic
Chemistry
Chemistry, Organic
Coupling
Oxidation
Physical Sciences
Science & Technology
Catalytic
Asymmetric
Oxidation
Coupling
Biaryl
Binaphthol
POLYMERS
ASYMMETRIC-SYNTHESIS
RESOLUTION
oxidation
coupling
REDUCTION
2-NAPHTHOLS
binaphthol
BINAPHTHOL DERIVATIVES
catalytic
1,1'-BINAPHTHYLS
asymmetric
biaryl
EFFICIENT
CATALYSTS
OXOVANADIUM(IV) COMPLEXES
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Summary: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. Graphical Abstracts
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.07.086