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

Y X Chen; L W Yang; Y M Li; Z Y Zhou; K H Lam; A S Chan; H L 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

Chirality. 2000 Jun;12(5-6):510-3. doi: 10.1002/(SICI)1520-636X(2000)12:5/6<510::AID-CHIR37>3.0.CO;2-E.

Authors

Y X Chen¹, L W Yang, Y M Li, Z Y Zhou, K H Lam, A S Chan, H L Kwong

Affiliation

¹ Open Laboratory of Chirotechnology and Department of Applied Biology and Chemical Technology, Hong Kong Polytechnic University, Hong Kong, China.

PMID: 10824179
DOI: 10.1002/(SICI)1520-636X(2000)12:5/6<510::AID-CHIR37>3.0.CO;2-E

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.