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Synlett 2023; 34(10): 1174-1184
DOI: 10.1055/a-1957-3872
DOI: 10.1055/a-1957-3872
cluster
Dispersion Effects
Reaction Mechanisms for Chiral-Phosphate-Catalyzed Transformations Involving Cationic Intermediates and Protic Nucleophiles
The research detailed in this account was funded by the University of British Columbia and the Natural Sciences and Engineering Research Council of Canada (NSERC).
Abstract
Recent strategies for enantioinduction often focus on employing a chiral catalyst to noncovalently interact with the substrate. By restricting the number of low energy diastereomeric transition states the reacting components can adopt, stereoselectivity can be achieved. Many of these noncovalent interactions include a significant dispersive component and these types of contacts have historically been difficult to model accurately. Modern computational methods have been designed to overcome such limitations. Using our computational work on chiral phosphate catalysis, we discuss the reasons for enantioselectivity in diverse reaction space.
1 Introduction
2 Chiral Phosphate Catalysis
3 Phosphate-Catalyzed Transfer Hydrogenation
4 Phosphate-Catalyzed Aza-Friedel–Crafts Reaction
5 Phosphate-Catalyzed Reactions Involving Allenamides
6 Comprehensive Qualitative Models
7 Chiral Phosphates and Thionium Intermediates
8 Conclusion
Key words
organocatalysis - enantioselectivity - chiral phosphoric acids - density functional theory - noncovalent interactionsPublication History
Received: 16 August 2022
Accepted after revision: 07 October 2022
Accepted Manuscript online:
07 October 2022
Article published online:
29 November 2022
© 2022. Thieme. All rights reserved
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