Organocatalytic Asymmetric Methodologies towards the Synthesis of Atropisomeric N-Heterocycles

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

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During the revision of this manuscript four relevant contributions appeared:
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