A concise synthesis of enantiomerically pure aroyl-l-alanines and dihydroaroyl-l-alanines

Abstract

AbstractStraightforward preparation of enantiomerically highly enriched N-substituted aroylalanines has been developed. This process involves the combination of crystallization-induced asymmetric transformation and a conjugate addition of N-nucleophiles to the corresponding aroylacrylic acids. Further transformations to 3,4-dichlorobenzoylalanine and aroyl-l-alanines via periodate oxidation and stereoselective reduction to N-substituted syn-4-aryl-4-hydroxy-2-aminobutanoic acids are also described.