4.7 Article

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

Journal

CHEMICAL COMMUNICATIONS
Volume 47, Issue 40, Pages 11204-11206

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c1cc11999k

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Funding

  1. Hong Kong Research Grants Council [HKU/CRF/01/08, HKU 700810]
  2. University Grants Committee of the Hong Kong Special Administrative Region, China [AoE 10/01P]

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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.

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