In this article, the functions of hydrogen bonds in organocatalytic reactions are discussed on atomic level by presenting
DFT studies of selected examples. Theoretical investigation provides a detailed insight in the mechanism of substrate activation
and orientation, and the stabilization of transition states and intermediates by hydrogen bonding (e.g. oxyanion hole). The
examples selected comprise stereoselective catalysis by bifunctional thioureas, solvent catalysis by fluorinated alcohols
in epoxidation by hydrogen peroxide, and intramolecular cooperative hydrogen bonding in TADDOL-type catalysts.
DFT studies of selected examples. Theoretical investigation provides a detailed insight in the mechanism of substrate activation
and orientation, and the stabilization of transition states and intermediates by hydrogen bonding (e.g. oxyanion hole). The
examples selected comprise stereoselective catalysis by bifunctional thioureas, solvent catalysis by fluorinated alcohols
in epoxidation by hydrogen peroxide, and intramolecular cooperative hydrogen bonding in TADDOL-type catalysts.
- Content Type Book Chapter
- DOI 10.1007/128_2009_3
- Authors
- Kerstin Etzenbach-Effers, University of Cologne Department of Chemistry Greinstrasse 4 50939 Cologne Germany
- Albrecht Berkessel, University of Cologne Department of Chemistry Greinstrasse 4 50939 Cologne Germany
- Book Series Topics in Current Chemistry
- Online ISSN 1436-5049
- Print ISSN 0340-1022
- Book Series Volume Volume 291/2009
- Book Asymmetric Organocatalysis
- DOI 10.1007/978-3-642-02815-1
- Print ISBN 978-3-642-02814-4