Hypervalent Iodine Oxidation of α,βUnsaturated Carbonyl Compounds

Yasumitsu Tamura, Takayuki Yakura, Hiroaki Terashi, Jun Ichi Haruta, Yasuyuki Kita

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Oxidation of non-enolizable α,β-unsaturated carbonyl compounds and enolizable β-monosubstituted α,β-unsaturated carbonyl compounds with phenyl iodine(III) diacetate (PIDA) in methanolic potassium hydroxide gave α-hydroxydimethylacetal β-methoxy products, and oxidation of enolizable β,β-disubstituted α,β-unsaturated carbonyl compounds under the same conditions gave α’-hydroxy products.

Original languageEnglish
Pages (from-to)570-577
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume35
Issue number2
DOIs
StatePublished - 1987

Keywords

  • methanolic potassium hydroxide solution
  • oxidation of α,β-unsaturated carbonyl compound
  • phenyl iodine(III) diacetate
  • α-hydroxydimethylacetal β-methoxy product
  • α’-hydroxy-α,β-unsaturated ketone

ASJC Scopus subject areas

  • General Chemistry
  • Drug Discovery

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