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Synlett 1995; 1995(6): 619-621
DOI: 10.1055/s-1995-5026
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Homochiral Proline N-Oxides as Conformational Constraints in Peptide Like Molecules

Ian A. O’Neil* , Neil D. Miller, Jim V. Barkley, Caroline M. R. Low, S. Barret Kalindjian
  • *Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, U.K.
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Publication Date:
31 December 2000 (online)

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The preparation of a number of N-alkylated proline derivatives which bear hydrogen bond donors in both the carboxyamide side chain and the N-substituent is described. Oxidation with m-CPBA gives homochiral amine oxides where the amine oxide configuration is determined by the proline side chain NH group. The amine oxides are stabilized by the presence of two intramolecular hydrogen bonds. These initial results have been extended to the preparation of homochiral tripeptide like molecules.

Homochiral Amine Oxides - Hydrogen Bonding - Peptide