A new practical method for the osmium-catalyzed dihydroxylation of olefins using bleach as the terminal oxidant

Gerald M. Mehltretter, Santosh Bhor, Markus Klawonn, Christian Döbler, Uta Sundermeier, Markus Eckert, Hans Christian Militzer, Matthias Beller

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23 Scopus citations

Abstract

A general procedure for the osmium-catalyzed dihydroxylation of various olefins using bleach as oxidant is reported for the first time. Aromatic and aliphatic olefins yield the corresponding cis-1,2-diols in the presence of dihydroquinine or dihydroquinidine derivatives (Sharpless ligands) with good to excellent chemo- and enantioselectivities under optimized pH conditions. In the presence of a small excess of bleach as reoxidant fast dihydroxylation takes place even at 0°C. Under optimum reaction conditions it is possible to dihydroxylate terminal aliphatic and aromatic olefins as well as internal olefins. The low price of the oxidant and the simple handling of bleach make this dihydroxylation variant attractive for further applications.

Original languageEnglish
Pages (from-to)295-301
Number of pages7
JournalSynthesis
Issue number2
DOIs
StatePublished - 2003
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Dihydroxylation
  • Homogenous catalysis
  • Osmium
  • Oxidations

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