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

doi:10.1016/j.tet.2004.07.086

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

College of Science

Research output: Contribution to journal › Article › peer-review

51 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 language	English
Pages (from-to)	9037-9042
Number of pages	6
Journal	Tetrahedron
Volume	60
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2004.07.086
Publication status	Published - 2004 Oct 4

Keywords

Asymmetric
Biaryl
Binaphthol
Catalytic
Coupling
Oxidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.07.086

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

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.",

keywords = "Asymmetric, Biaryl, Binaphthol, Catalytic, Coupling, Oxidation",

author = "Kim, {Kyoung Hoon} and Lee, {Dae Woong} and Lee, {You Sang} and Ko, {Dong Hyun} and Ha, {Deok Chan}",

note = "Funding Information: This work was financially supported by the Center for Molecular Design and Synthesis (CMDS) at KAIST. ",

year = "2004",

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doi = "10.1016/j.tet.2004.07.086",

language = "English",

volume = "60",

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journal = "Tetrahedron",

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TY - JOUR

T1 - Enantioselective oxidative coupling of methyl 3-hydroxy-2-naphthoate using mono-N-alkylated octahydrobinaphthyl-2,2′-diamine ligand

AU - Kim, Kyoung Hoon

AU - Lee, Dae Woong

AU - Lee, You Sang

AU - Ko, Dong Hyun

AU - Ha, Deok Chan

N1 - Funding Information: This work was financially supported by the Center for Molecular Design and Synthesis (CMDS) at KAIST.

PY - 2004/10/4

Y1 - 2004/10/4

N2 - 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.

AB - 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.

KW - Asymmetric

KW - Biaryl

KW - Binaphthol

KW - Catalytic

KW - Coupling

KW - Oxidation

UR - http://www.scopus.com/inward/record.url?scp=4444337349&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.07.086

DO - 10.1016/j.tet.2004.07.086

M3 - Article

AN - SCOPUS:4444337349

SN - 0040-4020

VL - 60

SP - 9037

EP - 9042

JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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