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Asymmetrische Katalyse durch chirale Wasserstoffbrückendonoren
Abstract
Wasserstoffbrücken bestimmen die Struktur eines großen Teils der uns umgebenden Materie. Die ungewöhnlichen Eigenschaften von flüssigem Wasser, die Faltung von Proteinen zu stabilen dreidimensionalen Strukturen, die DNA‐Basenpaarung und die Bindung von Liganden an Rezeptoren beruhen auf dieser nichtkovalenten Wechselwirkung. Neben ihrer strukturgebenden Rolle haben Wasserstoffbrücken auch entscheidende Funktionen bei katalytischen Prozessen. Enzyme beschleunigen viele biochemische Reaktionen, indem sie die Elektronendichte eines Elektrophils durch Bildung einer Wasserstoffbrücke verringern und es so für den nucleophilen Angriff aktivieren. In der organischen Synthese hat man das Potenzial dieser Strategie erkannt, und niedermolekulare Verbindungen, insbesondere chirale Wasserstoffbrückendonoren, wurden als Katalysatoren für enantioselektive Synthesen entwickelt. Dieser Aufsatz zeigt, welche strukturellen und mechanistischen Merkmale in wasserstoffbrückenvermittelten Katalyseprozessen zu hohen Enantioselektivitäten führen.
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Citations
Cited by
Asymmetric Aminocatalysis—Gold Rush in Organic Chemistry
Melchiorre, P., Marigo, M., Carlone, A., & Bartoli, G. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705523 · Cited by 1,256
Nonlinear Effects in Asymmetric Catalysis
Satyanarayana, T., Abraham, S., & Kagan, H. B. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200705241 · Cited by 591
Albrecht, Ł., Jiang, H., & Jørgensen, K. A. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201102522 · Cited by 466
Asymmetrische Organokatalyse: Eintritt in die Reifezeit
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie · doi:10.1002/ange.200704684 · Cited by 398
Whiteoak, C. J., Nova, A., Maseras, F., & Kleij, A. W. (2012) · ChemSusChem · doi:10.1002/cssc.201200255 · Cited by 339
Metadata
- Authors
- Taylor, M. S., & Jacobsen, E. N.
- Venue
- Angewandte Chemie
- Publisher
- Wiley
- Published
- 2006-02-21
- Volume
- 118
- Issue
- 10
- Pages
- 1550-1573
- ISSN
- 0044-8249 (ISSN-L)
- 1521-3757
- OpenAlex
- W2168204348
- Cited by
- 564
- References
- 0
- FWCI
- 32.50
- Type
- journal article
- Language
- de
- Open access
- closed
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