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Synlett 1995; 1995(6): 617-618
DOI: 10.1055/s-1995-5027
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The Synthesis of Proline Derived Homochiral Amine Oxides

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 oxidation of a number of N-benzyl proline derivatives is described. The oxidation proceeds with complete diastereoselectivity to give homochiral amine oxides when a hydrogen bond donor group is located in the proline carboxylate side chain. The product amine oxides are highly stable, crystalline compounds. In all cases, the amine oxide is formed syn to the hydrogen bonding donor group.

Homochiral Amine Oxides - Hydrogen Bonding