Asymmetric Induction and Amplification in Stereodynamic Catalytic Systems by Noncovalent Interactions

In memoriam of Prof. Dr. Kilian Muñiz (1970–2020)

Abstract

The local transmission of chiral information by noncovalent interactions is one of the most fundamental processes broadly found in nature, i.e. in complex biochemical systems. This review summarizes our accomplishments in investigating chiral induction in stereodynamic ligands and catalysts by weak intermolecular interactions. It includes our efforts to characterize numerous stereodynamic compounds in detail with respect to their thermodynamic and kinetic properties. Furthermore, many stereolabile ligands for enantioselective catalysis are described, where directed stereoinduction afforded highly enantio- or diastereoenriched catalysts for subsequent selective asymmetric transformations. Various approaches for the dynamic enrichment of one of the catalyst’s conformers are presented, such as noncovalent interaction of the ligand with a chiral environment or a chiral solute. Finally, successful chemical systems are presented in which a process of chiral induction can be coupled with an autoinductive mechanism triggered by the chirality of its own reaction product, realizing Nature-inspired feedback loops resulting in self-amplifying, enantioselective catalytic reactions.

1 Introduction

2 Mapping the Stereodynamic Landscape

3 Chiral Induction by Noncovalent Interactions

4 Autoinduction and Chiral Amplification

5 Self-Alignment and Emergence of Chirality

6 Conclusion

Key words

asymmetric catalysis - ligand design - noncovalent interactions - chiral induction - chiral amplification

Publication History

Received: 15 September 2020

Accepted after revision: 29 September 2020

Accepted Manuscript online:
29 September 2020

Article published online:
02 November 2020

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