Synthesis of a new chiral ligand, 6,6'-dihydroxy-5, 5'-biquinoline (BIQOL) and its applications in the asymmetric addition of diethylzinc to aldehydes

Yi Xin Chen; Li Wei Yang; Yue Ming Li; Zhong Yuan Zhou; Kim Hung Lam; Albert S.C. Chan; Hoi Lun Kwong

doi:10.1002/(SICI)1520-636X(2000)12:5/6<510::AID-CHIR37>3.0.CO;2-E

Synthesis of a new chiral ligand, 6,6'-dihydroxy-5, 5'-biquinoline (BIQOL) and its applications in the asymmetric addition of diethylzinc to aldehydes

Yi Xin Chen, Li Wei Yang, Yue Ming Li, Zhong Yuan Zhou, Kim Hung Lam, Albert S.C. Chan, Hoi Lun Kwong

Research output: Journal article publication › Journal article › Academic research › peer-review

21 Citations (Scopus)

Abstract

A new chiral ligand 6, 6'-dihydroxy-5, 5'-biquinoline (BIQOL, 2) was prepared via Cu²⁺ mediated coupling. The resolution was carried out by separating the corresponding ditrifluomethanesulfonate on chiral column. When applied to the enantioselective addition of diethylzinc to aromatic aldehydes, this ligand induced the reaction with enantioselectivity equivalent to that induced by BINOL. The effects of solvent and reaction temperature on enantioselectivity were also studied. (C) 2000 Wiley-Liss, Inc.

Original language	English
Pages (from-to)	510-513
Number of pages	4
Journal	Chirality
Volume	12
Issue number	5-6
DOIs	https://doi.org/10.1002/(SICI)1520-636X(2000)12:5/6<510::AID-CHIR37>3.0.CO;2-E
Publication status	Published - 1 Jan 2000

Keywords

BINOL
BIQOL
Diethylzinc
Quinoline

ASJC Scopus subject areas

Analytical Chemistry
Catalysis
Pharmacology
Drug Discovery
Spectroscopy
Organic Chemistry

More information

10.1002/(SICI)1520-636X(2000)12:5/6<510::AID-CHIR37>3.0.CO;2-E

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title = "Synthesis of a new chiral ligand, 6,6'-dihydroxy-5, 5'-biquinoline (BIQOL) and its applications in the asymmetric addition of diethylzinc to aldehydes",

abstract = "A new chiral ligand 6, 6'-dihydroxy-5, 5'-biquinoline (BIQOL, 2) was prepared via Cu2+ mediated coupling. The resolution was carried out by separating the corresponding ditrifluomethanesulfonate on chiral column. When applied to the enantioselective addition of diethylzinc to aromatic aldehydes, this ligand induced the reaction with enantioselectivity equivalent to that induced by BINOL. The effects of solvent and reaction temperature on enantioselectivity were also studied. (C) 2000 Wiley-Liss, Inc.",

keywords = "BINOL, BIQOL, Diethylzinc, Quinoline",

author = "Chen, {Yi Xin} and Yang, {Li Wei} and Li, {Yue Ming} and Zhou, {Zhong Yuan} and Lam, {Kim Hung} and Chan, {Albert S.C.} and Kwong, {Hoi Lun}",

year = "2000",

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doi = "10.1002/(SICI)1520-636X(2000)12:5/6<510::AID-CHIR37>3.0.CO;2-E",

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TY - JOUR

T1 - Synthesis of a new chiral ligand, 6,6'-dihydroxy-5, 5'-biquinoline (BIQOL) and its applications in the asymmetric addition of diethylzinc to aldehydes

AU - Chen, Yi Xin

AU - Yang, Li Wei

AU - Li, Yue Ming

AU - Zhou, Zhong Yuan

AU - Lam, Kim Hung

AU - Chan, Albert S.C.

AU - Kwong, Hoi Lun

PY - 2000/1/1

Y1 - 2000/1/1

N2 - A new chiral ligand 6, 6'-dihydroxy-5, 5'-biquinoline (BIQOL, 2) was prepared via Cu2+ mediated coupling. The resolution was carried out by separating the corresponding ditrifluomethanesulfonate on chiral column. When applied to the enantioselective addition of diethylzinc to aromatic aldehydes, this ligand induced the reaction with enantioselectivity equivalent to that induced by BINOL. The effects of solvent and reaction temperature on enantioselectivity were also studied. (C) 2000 Wiley-Liss, Inc.

AB - A new chiral ligand 6, 6'-dihydroxy-5, 5'-biquinoline (BIQOL, 2) was prepared via Cu2+ mediated coupling. The resolution was carried out by separating the corresponding ditrifluomethanesulfonate on chiral column. When applied to the enantioselective addition of diethylzinc to aromatic aldehydes, this ligand induced the reaction with enantioselectivity equivalent to that induced by BINOL. The effects of solvent and reaction temperature on enantioselectivity were also studied. (C) 2000 Wiley-Liss, Inc.

KW - BINOL

KW - BIQOL

KW - Diethylzinc

KW - Quinoline

UR - http://www.scopus.com/inward/record.url?scp=0034037059&partnerID=8YFLogxK

U2 - 10.1002/(SICI)1520-636X(2000)12:5/6<510::AID-CHIR37>3.0.CO;2-E

DO - 10.1002/(SICI)1520-636X(2000)12:5/6<510::AID-CHIR37>3.0.CO;2-E

M3 - Journal article

AN - SCOPUS:0034037059

SN - 0899-0042

VL - 12

SP - 510

EP - 513

JO - Chirality

JF - Chirality

IS - 5-6

ER -

Synthesis of a new chiral ligand, 6,6'-dihydroxy-5, 5'-biquinoline (BIQOL) and its applications in the asymmetric addition of diethylzinc to aldehydes

Abstract

Keywords

ASJC Scopus subject areas

More information

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