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Synthesis 2020; 52(17): 2450-2468
DOI: 10.1055/s-0040-1707814
short review
© Georg Thieme Verlag Stuttgart · New York

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
Further Information

Publication History

Received: 17 February 2020

Accepted after revision: 28 April 2020

Publication Date:
15 June 2020 (online)

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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
 

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