Synlett, Inhaltsverzeichnis

Synlett 2022; 33(20): 1991-2003
DOI: 10.1055/a-1965-2928

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The Application of 2-Naphthols in Asymmetric Synthesis of Atropisomers

Shao-Hua Xiang‡

^aDepartment of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055, P. R. of China

^bAcademy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518055, P. R. of China

,

Jun Kee Cheng‡

^aDepartment of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055, P. R. of China

,

Bin Tan∗

^aDepartment of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055, P. R. of China

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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

Key words

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

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