Stereoselective organocatalytic oxidation of alcohols to enals: A homologation method to prepare polyenes

Xiaobei Chen, Yinan Zhang, Huixin Wan, Wei Wang, Shilei Zhang

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A novel method for organocatalytic oxidation through oxidative enamine catalysis was developed with excellent compatibility for the direct syntheses of enals from simple saturated alcohols. By using this amine-catalyzed IBX-oxidation, a wide range of aromatic and aliphatic substituted enals were successfully generated in high yields and exclusively stereoselective E-geometry. Moreover, varying the solvents and/or the loading amounts of IBX allowed for the selective oxidation of alcohols and aldehydes. Importantly, the homologous application of this method provided a selective and efficient way of preparing various highly sensitive conjugated polyene frameworks, which are enriched in natural products.

Original languageEnglish (US)
Pages (from-to)3532-3535
Number of pages4
JournalChemical Communications
Volume52
Issue number17
DOIs
StatePublished - Feb 28 2016
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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