Ruthenium-catalyzed asymmetric alkene epoxidation with tert-butyl hydroperoxide as oxidant

Santosh Bhor, Man Kin Tse, Markus Klawonn, Christian Döbler, Wolfgang Mägerlein, Matthias Beller

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

A ruthenium-catalyzed asymmetric epoxidation of various olefins using tert-butyl hydroperoxide (TBHP) as the oxidant is reported. By applying ruthenium(pyridinebisoxazoline)-(pyridinedicarboxylate) complexes 1 [Ru(pybox)(pydic), 1] as catalysts, aromatic and aliphatic olefins yielded the corresponding epoxides at room temperature in good to excellent yields and enantioselectivities up to 65% ee. Slow addition of the stoichiometric oxidant significantly improved the yield and the chemoselectivity of the reaction.

Original languageEnglish
Pages (from-to)263-267
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume346
Issue number2-3
DOIs
StatePublished - Feb 2004
Externally publishedYes

Keywords

  • Asymmetric catalysis
  • Epoxidation
  • Homogeneous catalysis
  • N,O ligands
  • Ruthenium
  • Tert-butyl hydroperoxide

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