Chiral bioinspired non-heme iron complexes for enantioselective epoxidation of α,β-unsaturated ketones

Mei Wu, Cheng Xia Miao, Shoufeng Wang, Xiaoxue Hu, Chungu Xia, Fritz E. Kühn, Wei Sun

Research output: Contribution to journalArticlepeer-review

107 Scopus citations

Abstract

Chiral bioinspired iron complexes of N4 ligands based on the ethylenediamine backbone display remarkable levels of enantioselectivity for the first time in the asymmetric epoxidation of α,β-unsaturated ketones using hydrogen peroxide (up to 87% ee) or peracetic acid as oxidant, respectively. Notablely, isotopic labeling with H218O strongly demonstrated that there is a reversible water binding step prior to generation of the significant intermediate. Besides, the complex [L 2Fe(III)2(μ-O)(μ-CH3CO2)] 3+ usually derived from the decay of the LFe(IV)=O species or thermodynamic sinks for a number of iron complexes was identified by HR-MS. In addition, the possible mechanisms were proposed and LFe(V)=O species may be the main active intermediate in the catalytic system.

Original languageEnglish
Pages (from-to)3014-3022
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number16
DOIs
StatePublished - Nov 2011

Keywords

  • α,β-unsaturated carbonyl compounds
  • chiral N ligand
  • enantioselectivity
  • epoxidation
  • iron

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