Organocatalytic Asymmetric Methodologies towards the Synthesis of Atropisomeric N-Heterocycles

Vasco Corti; Giulio Bertuzzi

doi:10.1055/s-0040-1707814

Synthesis, Table of Contents

Synthesis 2020; 52(17): 2450-2468
DOI: 10.1055/s-0040-1707814

short review

Organocatalytic Asymmetric Methodologies towards the Synthesis of Atropisomeric N-Heterocycles

Vasco Corti ∗

,

Giulio Bertuzzi ∗

Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark Email: vasco@chem.au.dk Email: gibe@chem.au.dk

› Author Affiliations

Abstract

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Abstract

A perspective on the literature dealing with the organocatalytic asymmetric preparation of axially chiral N-heterocycles is provided. A particular focus is devoted to rationalize the synthetic strategies employed in each case. Moreover, specific classes of organocatalysts are shown to stand out as privileged motives for the stereoselective preparation of such synthetically challenging molecular architectures. Finally, an overview of the main trends in the field is given.

1 Introduction

2 Five-Membered Rings

2.1 Arylation

2.2 Dynamic Kinetic Resolution

2.3 Ring Construction

2.4 Central-to-Axial Chirality Conversion and Chirality Transfer

2.5 Desymmetrization

3 Six-Membered Rings

3.1 Desymmetrization

3.2 (Dynamic) Kinetic Resolution

3.3 Ring Construction

3.4 Central-to-Axial Chirality Conversion

4 Conclusion

Key words

heterocycles - atropisomerism - organocatalysis - indole - pyrrole - pyridine - quinoline

Full Text

References

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