Chiroptical properties of N-acetoacetyl-α-amino-acids, -amino-alcohols, and -amines

Abstract

N-Acetoacetyl derivatives of aliphatic and aromatic (S)-α-amino-acids exhibit enantiomorphic c.d. spectra in ethanolic potassium hydroxide. However, the c.d. spectra of both aliphatic and aromatic series are similar in a series of organic solvents. Similar c.d. behaviour is observed for aliphatic and aromatic N-acetoacetyl (S)-α-amino-alcohols and (S)-amines. Chiral shift reagent n.m.r. studies reveal that the N-acetoacetyl amino-acids are optically pure.