Chiral aminonaphthol-catalyzed enantioselective carbonyl addition of diethylzinc to aromatic aldehydes high-throughput screened by CD-HPLC analysis.

Ling Xu, Xiumin Shen, Cong Zhang, Koichi Mikami

Index: Chirality 17(8) , 476-80, (2005)

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Abstract

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).