Reaction Mechanisms for Chiral-Phosphate-Catalyzed Transformations Involving Cationic Intermediates and Protic Nucleophiles

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 interactions

Publikationsverlauf

Eingereicht: 16. August 2022

Angenommen nach Revision: 07. Oktober 2022

Accepted Manuscript online:
07. Oktober 2022

Artikel online veröffentlicht:
29. November 2022

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