Review
doi: 10.1007/978-3-642-02815-1_3.
Noncovalent organocatalysis based on hydrogen bonding: elucidation of reaction paths by computational methods
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- PMID: 21494946
- DOI: 10.1007/978-3-642-02815-1_3
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Review
Noncovalent organocatalysis based on hydrogen bonding: elucidation of reaction paths by computational methods
Top Curr Chem.
2010.
Abstract
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.
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