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Synlett 2022; 33(20): 1991-2003
DOI: 10.1055/a-1965-2928
DOI: 10.1055/a-1965-2928
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The Application of 2-Naphthols in Asymmetric Synthesis of Atropisomers
We are grateful for financial support from National Key Research and Development Program of China (2021YFF0701604), the National Natural Science Foundation of China (22231004, 22271135), Guangdong Innovative Program (2019BT02Y335), and Shenzhen Special Funds (JCYJ20210324120205016, JCYJ20210324105005015).
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 arenesPublikationsverlauf
Eingereicht: 21. September 2022
Angenommen nach Revision: 20. Oktober 2022
Accepted Manuscript online:
20. Oktober 2022
Artikel online veröffentlicht:
21. November 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
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