Synthesis of New Optically Active and Racemic Phenylsuccinamic Acids

Abstract

The synthesis, isolation, and characterization of new (S)-(+)- and racemic phenylsuccinamic acids, obtained from the reaction of (S)-(+)-phenylsuccinic anhydride (1) with five different primary amines (2a-e) is described. Ring opening of anhydride 1 led to the formation of two isomeric phenylsuccinamic acid products with the phenyl substituent b to the amide function being the preferred product. Complete racemization occurred with all of the a-phenylsuccinamic acids (3a-e) and β-phenylsuccinamic acids 4b and 4c. However, b-phenylsuccinamic acids 4a, 4d, and 4e were found to be optically active.

Key words

anhydride - chirality - nucleophilic addition - racemization - ring opening

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12

This method for the separation of a- and b-phenyl-succinamic acid was first reported in ref.⁸