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 synth...

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Bibliographic Details
Published in:Synlett 2022-12, Vol.33 (20), p.1991-2003
Main Authors: Xiang, Shao-Hua, Cheng, Jun Kee, Tan, Bin
Format: Article
Language:English
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Summary: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
ISSN:0936-5214
1437-2096
DOI:10.1055/a-1965-2928