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A New Approach to the Design of Heterogeneous Single-Site Enantioselective Catalysts

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Abstract

We analyze the merits of an approach to the design of enantioselective catalysts that relies on constraining an anchored organometallic complex at the inner walls of mesoporous silica. Two distinct metal centers {Rh(I) and Pd(II)}, three distinct diamino ligands {(S)-(-)-2-aminomethyl-1-ethylpyrrolidine, (AMP), (S)-(+)-(2-pyrrolidinyl-methyl)pyrrolidine, (PMP), and (1R,2R)-(+)-1,2-diphenylethylenediamine, (DED)}, two distinct methods of anchoring (a covalent and a noncovalent one), and two specific examples of enantioselective hydrogenation (the asymmetric hydrogenation of the C=C bond in E-α-phenylcinnamic acid and the asymmetric hydrogenation of the C=O bond in methyl benzoylformate) have been investigated. Values of enantiomeric excess (ee) ranging from a low of 66 to a high of 93 have been achieved by this approach. Moreover, the catalysts are robust and stand up well to recycling.

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Authors and Affiliations

  1. Department of Chemistry, Cambridge University, Lensfield Road, Cambridge, CB2 1EW, UK

    Matthew D. Jones, Robert Raja & Brian F.G. Johnson

  2. Davy Faraday Research Laboratory, The Royal Institution of Great Britain, 21 Albemarle Street, London, W1S 4BS, UK

    John Meurig Thomas

  3. Department of Materials Science and Metallurgy, University of Cambridge, Pembroke Street, Cambridge, CB2 3QZ, UK

    John Meurig Thomas

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  1. Matthew D. Jones
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  4. Brian F.G. Johnson
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Jones, M.D., Raja, R., Meurig Thomas, J. et al. A New Approach to the Design of Heterogeneous Single-Site Enantioselective Catalysts. Topics in Catalysis 25, 71–79 (2003). https://doi.org/10.1023/B:TOCA.0000003099.40587.3a

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  • DOI: https://doi.org/10.1023/B:TOCA.0000003099.40587.3a

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