An Axially Chiral Quinoline-2-Carboxylic Acid-Cu Catalyst for Enantioselective Synthesis of <i>C</i><sub>2</sub>- and <i>C</i><sub>1</sub>-Symmetric BINOLs

The in situ dimeric coordination of two chiral ligands bearing quinoline-2-carboxylic acid units and substituted BINOL backbones with a copper ion generates a new chiral catalyst for oxidative homo- and cross-coupling of various 2-naphthols, enabling enantioselective synthesis of a broad range of highly useful diversely substituted <i>C</i><sub>2</sub>- and <i>C</i><sub>1</sub>-symmetric BINOLs in up to 96% yield with good to excellent enantioselectivities (up to 98:2 e.r.).

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-12
DOI
https://doi.org/10.1021/acs.joc.4c01421
Citations
3
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
0.75

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article

An Axially Chiral Quinoline-2-Carboxylic Acid-Cu Catalyst for Enantioselective Synthesis of C2- and C1-Symmetric BINOLs

Jun Xu, Zhipeng Zhang, Shouyi Cen, Ahui Shen et al.
3 citations
The Journal of Organic Chemistry
Axial and Atropisomeric Chirality Synthesis
0.75
article

An Axially Chiral Quinoline-2-Carboxylic Acid-Cu Catalyst for Enantioselective Synthesis of C2- and C1-Symmetric BINOLs

Jun Xu, Zhipeng Zhang, Shouyi Cen, Ahui Shen, Jun Gao
article en
3 citations

Abstract

The in situ dimeric coordination of two chiral ligands bearing quinoline-2-carboxylic acid units and substituted BINOL backbones with a copper ion generates a new chiral catalyst for oxidative homo- and cross-coupling of various 2-naphthols, enabling enantioselective synthesis of a broad range of highly useful diversely substituted <i>C</i><sub>2</sub>- and <i>C</i><sub>1</sub>-symmetric BINOLs in up to 96% yield with good to excellent enantioselectivities (up to 98:2 e.r.).

The Journal of Organic ChemistryVol. 89(17)
East China University of Science and Technology (CN)
National Natural Science Foundation of China, Science and Technology Commission of Shanghai Municipality, Recruitment Program of Global Experts, Project 211, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 33%
Axial and Atropisomeric Chirality Synthesis
0.75
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An Axially Chiral Quinoline-2-Carboxylic Acid-Cu Catalyst for Enantioselective Synthesis of <i>C</i><sub>2</sub>- and <i>C</i><sub>1</sub>-Symmetric BINOLs — Jun Xu, Zhipeng Zhang, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS