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CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1021-1036
DOI: 10.1055/s-0037-1611636
DOI: 10.1055/s-0037-1611636
short review
Conformational Dynamics in Asymmetric Catalysis: Is Catalyst Flexibility a Design Element?
J.M.C. acknowledges the support of the NSF Graduate Research Fellowship Program. M.S.S. thanks the NIH (1 R01 GM121383) for supporting this work.Further Information
Publication History
Received: 23 November 2018
Accepted: 28 November 2018
Publication Date:
08 January 2019 (online)
Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue
Abstract
Traditionally, highly selective low molecular weight catalysts have been designed to contain rigidifying structural elements. As a result, many proposed stereochemical models rely on steric repulsion for explaining the observed selectivity. Recently, as is the case for enzymatic systems, it has become apparent that some flexibility can be beneficial for imparting selectivity. Dynamic catalysts can reorganize to maximize attractive non-covalent interactions that stabilize the favored diastereomeric transition state, while minimizing repulsive non-covalent interactions for enhanced selectivity. This short review discusses catalyst conformational dynamics and how these effects have proven beneficial for a variety of catalyst classes, including tropos ligands, cinchona alkaloids, hydrogen-bond donating catalysts, and peptides.
1 Introduction
2 Tropos Ligands
3 Cinchona Alkaloids
4 Hydrogen-Bond Donating Catalysts
5 Peptide Catalysts
6 Conclusion
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