ChemInform Abstract: Synthesis of Enantiopure o-Hydroxybenzylamines by Stereoselective Reduction of 2-Imidoylphenols: Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes.

✍ Scribed by Gianni Palmieri

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199931026

✦ Synopsis

Synthesis of Enantiopure o-Hydroxybenzylamines by Stereoselective Reduction of 2-Imidoylphenols: Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes. -Enantiopure (R,R)-o-hydroxybenzylamines (II), obtained by diastereoselective reduction of the corresponding imidoylphenols (I) with NaBH 4 -CeCl 3 or NaBH(O-Ac) 3 , serve as stereoselective catalysts in the addition of Et 2 Zn to aromatic or aliphatic aldehydes (III) and (VI). The best results are obtained for the phenyl derivative (IIc) which furnishes the adducts (V) and (VII) in excellent yields and optical purity of above 70%. -(PALMIERI, GIANNI; Eur.