Organocatalytic one-pot oxidative cleavage of terminal diols to dehomologated carboxylic acids

Masatoshi Shibuya, Ryusuke Doi, Takuro Shibuta, Shun Ichiro Uesugi, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

37 Citations (Scopus)

Abstract

The organocatalytic one-pot oxidative cleavage of terminal 1,2-diols to one-carbon-unit-shorter carboxylic acids is described. The combination of 1-Me-AZADO (cat.), NaOCl (cat.), and NaClO2 caused smooth one-pot oxidative cleavage under mild conditions. A broad range of substrates including carbohydrates and N-protected amino diols were converted without epimerization. Terminal triols and tetraols respectively underwent cleavage of their C-2 and C-3 moieties to afford their corresponding two- and three-carbon-unit-shorter carboxylic acids.

Original languageEnglish
Pages (from-to)5006-5009
Number of pages4
JournalOrganic letters
Volume14
Issue number19
DOIs
Publication statusPublished - 2012 Oct 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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