NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides with high diastereoselectivity: a short route to (-)-cytoxazone and droxidopa

Shyla George, Srinivasarao V. Narina, Arumugam Sudalai

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The NaIO4-mediated asymmetric bromohydroxylation of α,β-unsaturated carboxamides was achieved using lithium bromide as the bromine source under acidic conditions at rt to afford the corresponding chiral α-bromo-β-hydroxy carboxamides. Excellent yields (77-90%) and diastereoselectivities (up to 10:1) along with exclusive control over regio- as well as anti-selectivity are the main features with a good scope of substrates. The method has successfully been applied in the enantioselective syntheses of two biologically important molecules, viz (-)-cytoxazone and l-threo-DOPS (droxidopa).

Original languageEnglish (US)
Pages (from-to)1375-1378
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number8
DOIs
StatePublished - Feb 19 2007

Bibliographical note

Funding Information:
S.G. and N.V.S. thank CSIR, New Delhi, for the award of research fellowships. The authors are thankful to Dr. B. D. Kulkarni, Deputy Director, for his support and encouragement.

Keywords

  • Asymmetric bromohydroxylation
  • Carboxamide
  • Cytoxazone
  • Droxidopa
  • NaIO

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