An improved version of the Sharpless asymmetric dihydroxylation

G. M. Mehltretter, C. Dobler, U. Sundermeier, M. Beller

Research output: Contribution to journalArticlepeer-review

55 Scopus citations


The osmium catalyzed asymmetric dihydroxylation of olefins (Sharpless AD) was studied under controlled pH conditions. It was found that providing a constant pH value of 12.0 leads to improved reaction rates for internal olefins. Hydrolysis aids such as methanesulfonamide can be omitted. For terminal olefins, working at a constant pH of 10.0 at room temperature leads to higher enantioselectivities compared to AD reactions without pH control. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)8083-8087
Number of pages5
JournalTetrahedron Letters
Issue number42
StatePublished - 14 Oct 2000
Externally publishedYes


  • Asymmetric dihydroxylations
  • Olefins
  • Osmium


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