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Synlett 1993; 1993(7): 515-518
DOI: 10.1055/s-1993-22513
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The Novel Use of Proline Derived Amine Oxides in Controlling Amide Conformation

Ian A. O'Neil* , Neil D. Miller, Julie Peake, 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, England
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Publication Date:
19 March 2002 (online)

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The oxidation of secondary amides derived from N-benzyl proline to the corresponding N-oxide proceeds with complete diastereoselectivity to give chiral amine oxides of high stability. The amine oxide is shown to be intramolecularly hydrogen bonded to the adjacent amide.