Osmium-Catalyzed Dihydroxylation of Olefins in Acidic Media

Old Process, New Tricks

Philippe Dupau, Robert Epple, Allen A Thomas, Valery V. Fokin, K. Barry Sharpless

Research output: Contribution to journalArticle

168 Citations (Scopus)

Abstract

A screen of over 500 diversely functionalized additives in osmium-catalyzed dihydroxylation has uncovered that electron-deficient olefins are converted into the corresponding diols much more efficiently when the pH of the reaction medium is maintained on the acidic side. Further studies have identified citric acid as the additive of choice, for it allows preparation of very pure diols in yields generally exceeding 90%. As described here, a much wider range of olefin classes can now be successfully dihydroxylated. The process is experimentally simple, in most cases involving little more than dissolving the reactants in water or a waler/tertbutyl alcohol mixture, stirring them, and filtering off the pure diol product.

Original languageEnglish (US)
Pages (from-to)421-433
Number of pages13
JournalAdvanced Synthesis and Catalysis
Volume344
Issue number3-4
DOIs
StatePublished - May 1 2002

Fingerprint

Osmium
Alkenes
Olefins
Citric acid
Citric Acid
Alcohols
Electrons
Water

Keywords

  • Alkenes
  • Dihydroxylations
  • Homogeneous catalysis
  • Osmium
  • Oxidations

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Osmium-Catalyzed Dihydroxylation of Olefins in Acidic Media : Old Process, New Tricks. / Dupau, Philippe; Epple, Robert; Thomas, Allen A; Fokin, Valery V.; Sharpless, K. Barry.

In: Advanced Synthesis and Catalysis, Vol. 344, No. 3-4, 01.05.2002, p. 421-433.

Research output: Contribution to journalArticle

Dupau, Philippe ; Epple, Robert ; Thomas, Allen A ; Fokin, Valery V. ; Sharpless, K. Barry. / Osmium-Catalyzed Dihydroxylation of Olefins in Acidic Media : Old Process, New Tricks. In: Advanced Synthesis and Catalysis. 2002 ; Vol. 344, No. 3-4. pp. 421-433.
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