The Application of 2-Naphthols in Asymmetric Synthesis of Atropisomers

Abstract

The venerable axially chiral biaryl skeletons used widely in asymmetric catalysis such as BINOLs, NOBINs, QUINOLs, and CPAs possess a 2-naphthol moiety or are derived from the naphthol precursor. The hydroxy functionality offers the interaction point or serves as functional handle for synthetic elaboration. This prevalence and significance drive our studies to incorporate this nucleophile class to fabricate an assortment of atropisomers. By activating the reacting partners via distinctive mechanisms, the arylation of quinones, azo- or nitroso-naphthalenes, VQM intermediates, 1,2,4-triazole-3,5-diones, isoquinolines, and 1-bromo-2-naphthols with 2-naphthols were successfully attained. A concise account of these developments is provided in this article.

1 Introduction

2 Asymmetric Arylation with Quinones

3 Asymmetric Arylation with Electron-Deficient Arenes

4 Asymmetric Synthesis of Atropisomers with other Electrophiles

5 Conclusion

Key words

atropisomers - 2-naphthols - asymmetric synthesis - organocatalysis - arylation - quinones - election-deficient arenes

Publication History

Received: 21 September 2022

Accepted after revision: 20 October 2022

Accepted Manuscript online:
20 October 2022

Article published online:
21 November 2022

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