(<i>S</i>,<i>S</i>)-2-(((Hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic Acid Methyl Ester

Abstract

The solvent-free Betti reaction of 2-naphthol, 4-nitrobenzaldehyde and (S)-valine methyl ester gave the corresponding aminobenzylnaphthol of the (S,S)-2-(((hydroxynaphth-1-yl)(4′-nitrophenyl)methyl)amino)-3-methylbutanoic acid methyl ester in good yield (59%). This product was fully characterized. We observed that the racemization that occurs in some Betti reactions with (S)-valine methyl ester was absent in this reaction, and thus the predominant (S,S)-product was obtained.

Keywords

• Betti reaction
• aminobenzylnaphthols
• chirality
• amino acids
• racemization
• solvent-free