Practical manganese-catalysed highly enantioselective cis-dihydroxylation of electron-deficient alkenes and detection of a cis-dioxomanganese(V) intermediate by high resolution ESI-MS analysis

Chem Commun (Camb). 2011 Oct 28;47(40):11204-6. doi: 10.1039/c1cc11999k. Epub 2011 May 26.

Abstract

A practical protocol has been developed for asymmetric cis-dihydroxylation of electron-deficient alkenes with Oxone catalysed by a manganese complex bearing a chiral tetradentate N(4)-donor ligand affording cis-diols in up to 95% yield with up to 96% ee. Analysis of the reaction mixture by high resolution ESI-MS revealed the formation of a cis-dioxomanganese(V) intermediate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Electrons*
  • Hydroxylation
  • Manganese / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Spectrometry, Mass, Electrospray Ionization*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Alkenes
  • Manganese