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Asymmetric dihydroxylation of C,C double bonds using catalytic amounts of osmium tetroxide, selenides, and air

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Keywords
  • Physical
  • Chemical
  • Mathematical & Earth Sciences :: Chemistry [G01]
  • Physique
  • Chimie
  • Mathématiques & Sciences De La Terre :: Chimie [G01]

Abstract

Selenides, selenoxides, osmium tetroxide, and potassium osmate dihydrate are in equilibrium in aqueous tert-butanol containing potassium carbonate. We took advantage of this feature to withdraw the equilibrium in each of the two directions to produce allylalcohols from allylselenides and diols from olefins. The latter reaction performed in the presence of catalytic amounts of Cinchona alkaloids and osmium tetroxide allows the enantioselective dihydroxylation of C,C double bonds.

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