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Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction

Vachal, Petr, Jacobsen, Eric N.·2002·Journal of the American Chemical Society

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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Metadata

Authors
Vachal, P., & Jacobsen, E. N.
Venue
Journal of the American Chemical Society
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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CoChat. (2026). Citation check: Structure-Based Analysis and Optimization of a Highly Enantioselective Catalyst for the Strecker Reaction. https://app.cochat.ai/papers/10.1021/ja027246j
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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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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.