Enantioselective borohydride reduction catalyzed by cobalt complexes: Discovery, analysis, and design for a halogen-free system

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Abstract

On the basis of a study on the enantioselective version of the oxidation-reduction hydration catalyzed by bis(1,3-diketonato)cobalt complexes, the highly enantioselective borohydride reduction of carbonyl compounds was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. The experimental and theoretical studies on the mechanistic insight of this reaction revealed that the key reactive intermediate of borohydride reduction catalyzed by ketoiminatocobalt(II) complexes would be the dichloromethyl-cobalt hydride with a sodium cation, which was generated from chloroform and sodium borohydride. The theoretical simulation of various axial groups in active cobalt complex catalysts predicted that the cobalt-carbene complexes could be employed as efficient catalysts. The newly designed complexes generated from cobalt complex and methyl diazoacetate made it possible to catalyze the enantioselective borohydride reduction in a completely halogen-free solvent.

Original languageEnglish
Article numberE21008SS
Pages (from-to)1628-1640
Number of pages13
JournalSynthesis
Issue number10
DOIs
Publication statusPublished - 2008 May 19

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Keywords

  • Aerobic oxidation
  • Asymmetric catalysts
  • Carbene complex
  • Cobalt complex
  • DFT method
  • Enantioselective reduction
  • Halogen-free solvent

ASJC Scopus subject areas

  • Organic Chemistry

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