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Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction
Abstract
A mechanistic investigation of the asymmetric Strecker reaction catalyzed by a metal-free Schiff base catalyst was conducted. The active site of the catalyst, the relevant stereoisomer of the imine substrate, and the solution structure of the imine-catalyst complex were elucidated using a series of kinetics, structure-activity, and NMR experiments. An unusual bridging interaction between the imine and the urea hydrogens of the catalyst was identified and supported by computation. Rational optimization of catalyst structure based on the mechanistic insight led to an improved catalyst for the asymmetric Strecker reaction.
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Cited by
Asymmetric Catalysis by Chiral Hydrogen‐Bond Donors
Taylor, M. S., & Jacobsen, E. N. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200503132 · Cited by 1,906
Self-citationAsymmetric Organocatalysis: From Infancy to Adolescence
Dondoni, A., & Massi, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200704684 · Cited by 1,252
Applications of Supramolecular Anion Recognition
Busschaert, N., Caltagirone, C., Van Rossom, W., & Gale, P. A. (2015) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00099 · Cited by 1,249
Kobayashi, S., Mori, Y., Fossey, J. S., & Salter, M. M. (2011) · Chemical Reviews · doi:10.1021/cr100204f · Cited by 988
Asymmetrische Organokatalyse: Eintritt in die Reifezeit
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Metadata
- Authors
- Vachal, P., & Jacobsen, E. N.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-08-01
- Volume
- 124
- Issue
- 34
- Pages
- 10012-10014
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2129718204
- Cited by
- 577
- References
- 0
- FWCI
- 22.73
- Type
- journal article
- Language
- en
- Open access
- closed
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- Vachal, P., & Jacobsen, E. N. (2002). Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction. Journal of the American Chemical Society. https://doi.org/10.1021/ja027246j
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