3-substituted BINOL Schiff bases and their reductive products for catalytic asymmetric addition of diethylzinc to aldehydes.
Three new chiral 3-substituted BINOL Schiff bases and their reductive 3-arylaminomethyl BINOL products have been synthesized and used for the asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium tetraisopropoxide. The reaction provided optically active secondary alcohols in high yield (86-100%) and good enantioselectivity (up to 92% ee).
Liu
Bing
B
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Dong
Zhi-Bing
ZB
Fang
Cao
C
Song
Hai-Bin
HB
Li
Jin-Shan
JS
D000447:Aldehydes / Q000737:chemistry; D007202:Indicators and Reagents; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; C406944:BINOL, naphthol; D007202:Indicators and Reagents; D008024:Ligands; D009284:Naphthols; D009942:Organometallic Compounds; D012545:Schiff Bases; C454811:diethylzinc