Synthesis of alpha-hydroxy ketones from terpene aldehydes

M Schueler, H Zorn, A M Z Slawin, R G Berger

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Unsymmetrically substituted alpha-hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to alpha,beta-unsaturated aldehydes and afforded the respective a-hydroxy-methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric alpha-hydroxy ketones have been resolved, and X-ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

Original languageEnglish
Pages (from-to)2591-2600
Number of pages10
JournalSynthetic Communications
Volume34
Issue number14
DOIs
Publication statusPublished - Jul 2004

Keywords

  • acyloins
  • alpha-hydroxy ketones
  • terpene aldehydes
  • cyanohydrin trimethylsilyl ethers
  • copper salt catalysis
  • nitriles
  • Grignard reaction
  • camphanates
  • tautomerisation
  • CYANOHYDRINS
  • BUTANOLIDES
  • KETIMINES
  • NITRILES
  • REAGENTS
  • AMINES

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