Asymmetric alpha-oxyacylation of cyclic ketones

Deborah Smithen, Christopher Mathews, Nick Tomkinson

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Reaction of cyclic ketones with chiral N-alkyl-O-acyl hydroxylamines leads to the corresponding α oxyacylated carbonyl compound in up to 89% e.e. The levels of asymmetric induction were influenced by solvent polarity, acid strength and, to a lesser extent, temperature. Increasing the steric bulk around the nitrogen atom of the hydroxylamine reagent led to increased levels of asymmetric induction, which was also found to be detrimental to the yield observed for the transformation. Examination of N and O substituents along with substrate revealed the scope and limitations of the procedure
Original languageEnglish
Pages (from-to)3756-3762
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume10
Issue number18
DOIs
Publication statusPublished - 11 Apr 2012

Keywords

  • cyclic ketones
  • solvent polarity
  • temperature
  • asymmetric induction

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