Chiral aminonaphthol-catalyzed enantioselective carbonyl addition of diethylzinc to aromatic aldehydes high-throughput screened by CD-HPLC analysis.
Optically active aminonaphthols derivatives are obtained by condensation of 2-naphthol, substituted benzaldehyde, and (S)-methylbenzylamine under mild conditions, without side products. Their absolute configurations are determined by X-ray crystallographic analysis. The addition of diethylzinc to aromatic aldehydes is considerably accelerated by the presence of a catalytic amount of crystalline to give, after hydrolysis, the corresponding 1-phenylpropanol in good enantiomeric purity, as determined by CD-HPLC analysis as HTPS (high-throughput screening).
Xu
Ling
L
Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan.
Shen
Xiumin
X
Zhang
Cong
C
Mikami
Koichi
K
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D008024:Ligands; D009284:Naphthols / Q000737:chemistry* / Q000145:classification; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D008024:Ligands; D009284:Naphthols; D009942:Organometallic Compounds; C454811:diethylzinc