Communication

Platinum-Catalyzed Asymmetric Hydrogenation: Spectroscopic Evidence for an O-H-O Hydrogen-Bond Interaction between Substrate and Modifier†

  1. Fabian Meemken1,
  2. Dr. Nobutaka Maeda1,*,
  3. Prof. Dr. Konrad Hungerbühler1,
  4. Prof. Dr. Alfons Baiker1,2,*

Article first published online: 27 JUN 2012

DOI: 10.1002/anie.201203007

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 33, pages 8212–8216, August 13, 2012

Additional Information

How to Cite

Meemken, F., Maeda, N., Hungerbühler, K. and Baiker, A. (2012), Platinum-Catalyzed Asymmetric Hydrogenation: Spectroscopic Evidence for an O-H-O Hydrogen-Bond Interaction between Substrate and Modifier . Angew. Chem. Int. Ed., 51: 8212–8216. doi: 10.1002/anie.201203007

Author Information

  1. 1

    Department of Chemistry and Applied Biosciences, Institute for Chemical and Bioengineering, Hönggerberg, HCI, 8093 Zürich (Switzerland) http://www.sust-chem.ethz.ch, www.baiker.ethz.ch

  2. 2

    Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia)

*Department of Chemistry and Applied Biosciences, Institute for Chemical and Bioengineering, Hönggerberg, HCI, 8093 Zürich (Switzerland) http://www.sust-chem.ethz.ch, www.baiker.ethz.ch

  1. †

    We thank Dr. Tamas Mallat (ETH Zurich) for valuable discussion.

Publication History

  1. Issue published online: 7 AUG 2012
  2. Article first published online: 27 JUN 2012
  3. Manuscript Received: 19 APR 2012

Funded by

  • ETH Zurich

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Keywords:

  • asymmetric hydrogenation;
  • IR spectroscopy;
  • diastereomeric complex;
  • heterogeneous catalysis;
  • modulation excitation spectroscopy
Thumbnail image of graphical abstract

The mighty cinchonidine: A diastereomeric surface complex in the asymmetric hydrogenation of ketopantolactone on chirally modified Pt is monitored by in situ ATR-IR spectroscopy, in combination with modulation excitation spectroscopy and phase-sensitive detection. Cinchonidine bound to the surface with its quinoline ring is shown to induce the chiral environment through a C9[BOND]O⋅⋅⋅H⋅⋅⋅O[DOUBLE BOND]C interaction (see scheme).

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