Polyol synthesis through hydrocarbon oxidation: De novo synthesis of L-galactose

Dustin J. Covell, Nicolaas A. Vermeulen, Nathan A. Labenz, M. Christina White

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) Carbohydrates from hydrocarbons : A hydrocarbon oxidation strategy for the synthesis of chiral polyols is validated by the enantioselective, de novo synthesis of differentially protected L-galactose (see scheme, TBS = tert-butyldimethylsilyl, Bn = benzyl). Key to this strategy is the selective C-H oxidation method for transforming protected chiral allylic alcohols into (E)-2-butene-1,4-diol derivatives.

Original languageEnglish (US)
Pages (from-to)8217-8220
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number48
DOIs
StatePublished - Dec 11 2006

Keywords

  • Allylic oxidation
  • C-H activation
  • Carbohydrates
  • Enantioselectivity
  • Polyols

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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