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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
Author(s) -
Chen YiXin,
Yang LiWei,
Li YueMing,
Zhou ZhongYuan,
Lam KimHung,
Chan Albert S.C.,
Kwong HoiLun
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<510::aid-chir37>3.0.co;2-e
Subject(s) - diethylzinc , chemistry , enantioselective synthesis , ligand (biochemistry) , chiral ligand , solvent , resolution (logic) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , receptor , biochemistry , artificial intelligence , computer science
A new chiral ligand 6, 6′‐dihydroxy‐5, 5′‐biquinoline (BIQOL, 2 ) was prepared via Cu 2+ 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. Chirality 12:510–513, 2000. © 2000 Wiley‐Liss, Inc.