Atroposelective synthesis of sterically hindered stereochemically complex BINOL derivatives

Yang Yang, Guishun Bai, Mengmeng Qin, Juelian Wang, Yihuan Yang, Hong Wang, Damien Bonne, Jean Rodriguez, Xiaoze Bao

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Article in Chemical science, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1citing papers in PubMed

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3 · Its place in the literature

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1 citing paper in PubMed.

Aqueous NaRSC advances · 2026
Article

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5 · Who and what money

Authors and funding

9 authors.

Yang YangCollege of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology Hangzhou 310014 China hongw@zjut.edu.cn baoxiaoze@zjut.edu.cn.

Guishun BaiCollege of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology Hangzhou 310014 China hongw@zjut.edu.cn baoxiaoze@zjut.edu.cn.

Mengmeng QinCollege of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology Hangzhou 310014 China hongw@zjut.edu.cn baoxiaoze@zjut.edu.cn.

Juelian WangCollege of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology Hangzhou 310014 China hongw@zjut.edu.cn baoxiaoze@zjut.edu.cn.

Yihuan YangCollege of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology Hangzhou 310014 China hongw@zjut.edu.cn baoxiaoze@zjut.edu.cn.

Hong WangCollege of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology Hangzhou 310014 China hongw@zjut.edu.cn baoxiaoze@zjut.edu.cn.ORCID https://orcid.org/0000-0003-0058-060X

Damien BonneAix Marseille Univ, CNRS, Centrale Med, iSm2 Marseille France damien.bonne@univ-amu.fr.ORCID https://orcid.org/0000-0003-4479-4626

Jean RodriguezAix Marseille Univ, CNRS, Centrale Med, iSm2 Marseille France damien.bonne@univ-amu.fr.

Xiaoze BaoCollege of Pharmaceutical Science & Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology Hangzhou 310014 China hongw@zjut.edu.cn baoxiaoze@zjut.edu.cn.ORCID https://orcid.org/0000-0003-3682-2674

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A sequential strategy is proposed for the atroposelective construction of new families of sterically hindered BINOL derivatives bearing multiple stereogenic elements and featuring up to four stereogenic centers. The sequence begins with an organocatalyzed regio- and enantioselective mono-dihydrobenzofurannulation of commercially available 2,7-dihydroxynaphthalene establishing two stereogenic carbon atoms, followed by highly atroposelective copper-catalyzed aerobic oxidative homo- or cross-couplings fixing the axial chirality thanks to a nearly perfect induction of chirality. In addition, the resulting BINOL derivatives serve as promising precursors for the synthesis of either complex spiroheterocycles by axial-to-central conversion of chirality, heterohelicene-like molecules by axial-to-helical conversion of chirality, or an atropisomeric naphtho[2,1-

Identifiers

PMID40988694

DOI10.1039/d5sc05212b

PMCPMC12452015

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