Monitoring interconversion between stereochemical states in single chirality-transfer complexes on a platinum surface

Publication: Research - peer-reviewJournal article

DOI

  • Guillaume Goubert
    Guillaume GoubertUniv Laval, Laval University, Dept Chem
  • Yi Dong
    Yi DongUniv Laval, Laval University, Dept Chem
  • Michael N. Groves
    Michael N. Groves
  • J.-C. Lemay
    J.-C. LemayUniv Laval, Laval University, Dept Chem
  • Bjork Hammer
  • Peter H. McBreen
    Peter H. McBreenUniv Laval, Laval University, Dept Chem

Elementary steps in enantioselective heterogeneous catalysis take place on the catalyst surface and the targeted synthesis of a desired enantiomer requires the implantation of chiral information at the surface, which can be achieved-for example-by adsorbing chiral molecules. Studies of the structures of complexes formed between adsorbed prochiral reagents and chiral molecules yield information on the forces exerting stereocontrol, but further insight could be gained by studying the dynamics of their interactions. Here, using time-lapsed scanning tunnelling microscopy and density functional theory, we observe coupling between multiple stereochemical states within individual non-covalently bonded chirality-transfer complexes on a metal surface. We identify two modes of transformation between stereochemical states and find that the prochiral reagent can sample several complexation geometries during the lifetime of a complex, switching between states of opposing prochirality in the process. These results provide insight on the contribution of individual stereochemical states to the overall enantioselectivity of reactions occurring on catalyst surfaces.

Original languageEnglish
JournalNature Chemistry
Volume9
Issue number6
Pages (from-to)531-536
Number of pages6
ISSN1755-4330
DOIs
StatePublished - Jun 2017

    Keywords

  • ASYMMETRIC HYDROGENATION, METAL-SURFACES, CATALYSIS, PT(111), ENANTIOSELECTIVITY, ADSORPTION, MOLECULES, KETONES, SITES, STM

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