Oxidative rearrangement of cyclic tertiary allylic alcohols with IBX in DMSO

Masatoshi Shibuya, Shinichiro Ito, Michiyasu Takahashi, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

66 Citations (Scopus)

Abstract

(Chemical Equation Presented) A practical and environmentally friendly method for oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by the IBX/DMSO reagent system is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are compatible under the reaction conditions prescribed.

Original languageEnglish
Pages (from-to)4303-4306
Number of pages4
JournalOrganic letters
Volume6
Issue number23
DOIs
Publication statusPublished - 2004 Nov 11

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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