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Synthesis 1991; 1991(11): 989-993
DOI: 10.1055/s-1991-26625
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Oxygen Alkylation of Schiff Base Derivatives of Amino Acids

Martin J. O'Donnell* , Gwendolyn K. Cook, David B. Rusterholz
  • *Department of Chemistry, Indiana University-Purdue University at Indianapolis, Indianapolis, IN 46205, USA
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Publication Date:
29 April 2002 (online)

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Higher imine esters 1a-h and 7a-b of amino acids and dipeptides are prepared in 68-91% yield by saponification of the benzophenone Schiff base methyl esters 3a-d and 6 using phase-transfer techniques followed by O-alkylation with an alkyl halide. The procedure occurs with retention of configuration at the α-carbon except with phenylglycine derivatives.