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DOI: 10.1055/s-2002-19294
Synthesis of New Optically Active and Racemic Phenylsuccinamic Acids
Publication History
Publication Date:
04 August 2004 (online)
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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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References
This method for the separation of a- and b-phenyl-succinamic acid was first reported in ref.8