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Synthesis 2002(1): 0047-0052
DOI: 10.1055/s-2002-19294
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of New Optically Active and Racemic Phenylsuccinamic Acids

R. Stephani*, V. Cesare, I. Sadarangani, I. Lengyel
Department of Chemistry, St. John"s University , Jamaica, New York, 11439, USA
Fax: +1(718)9901876; e-Mail: stephanr@stjohns.edu;
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Publication History

Received 15 April 2001
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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This method for the separation of a- and b-phenyl-succinamic acid was first reported in ref.8