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

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

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 115 KB
Volume: 12
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<510::aid-chir37>3.0.co;2-e

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✦ Synopsis

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.