The origin of enantioselectivity for intramolecular Friedel–Crafts reaction catalyzed by supramolecular Cu/DNA catalyst complex

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Abstract

The present theoretical investigation aims at understanding the origin of enantioselectivity of intramolecular Friedel–Crafts reaction, catalyzed by supramolecular Cu/DNA catalyst. 28 Conformations of the supramolecular L-Cu(II)-R/d(CAAAAATTTTTG)2 complex were thoroughly modeled to estimate their stability and structural features depending on the metal complex conformation and its intercalation position. The preferred formation of S-product can be rationalized by the higher binding energy of pro-S conformations to DNA. Pro-S conformations are structurally closer to the expected C3–C2′ bond formation TS and usually not deeply buried into DNA, which would facilitate TS formation by decreasing the energy for conformational changes.

Journal

  • Chemical Physics Letters

    Chemical Physics Letters (600), 87-95, 2014-04-29

    Elsevier B.V.

Codes

  • NII Article ID (NAID)
    120005439185
  • NII NACSIS-CAT ID (NCID)
    AA00602122
  • Text Lang
    ENG
  • Article Type
    journal article
  • ISSN
    0009-2614
  • Data Source
    IR 
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