Selective Oxidation of Polyfunctional 2-Amino-1,3-propanediol Derivatives

Zixing Shan* and Guojian Lu
Department of Chemistry, Wuhan University, Wuhan 430072, China kenshan@public.wh.hb.cn
J. Org. Chem., 2004, 69 (10), pp 3593–3594
DOI: 10.1021/jo049973y
Publication Date (Web): April 20, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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Oxidation of polyfunctional threo-(1S,2S)-2-amino-1,3-propanediol derivatives with a 717 anion-exchange resin-supported bromine has been investigated. The result showed that oxidized products were in close relationship with the substituents at nitrogen in the starting materials. Its primary and secondary amine derivatives were oxidized in the presence of Na2HPO4 to give essentially a substituted chiral oxazoline or C(3)−O acylated product in high yield, while oxidation of its N,N-dimethyl derivative mainly gave a chiral N-methyl oxidation−formylation product. This selective oxidation was first observed in 2-amino-1,3-propanediol chemistry.

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History

  • Published In Issue May 14, 2004
  • Received January 2, 2004

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