Construction of planar chiral [2,2]paracyclophanes via photoinduced cobalt-catalyzed desymmetric addition

Planar chiral [2,2]paracyclophanes (PCPs) are widely used in materials science and asymmetric syntheses. Therefore, synthetic and material chemists have focused on the efficient and selective construction of planar chiral PCPs for decades. Herein, we present a photoinduced cobalt-catalyzed desymmetric addition of pseudo-para-diformyl and pseudo-gem-diformyl PCP, enabling the synthesis of planar chiral PCP alcohols with both planar and central chiralities. This method delivers 48 examples with yields up to 87%, diastereomeric ratios greater than 19:1, and an enantiomeric excess exceeding 99%. This protocol provides a original and efficient approach for the synthesis of planar chiral PCPs.

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Publication Details

Journal
Nature Communications
Published
2025-04-29
DOI
https://doi.org/10.1038/s41467-025-59089-3
Citations
10
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
9.36

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article

Construction of planar chiral [2,2]paracyclophanes via photoinduced cobalt-catalyzed desymmetric addition

Ke Gao, Wenhan Xu, Liang‐Qiu Lu, Wei Xiong et al.
10 citations
Nature Communications
Synthesis and Properties of Aromatic Compounds
9.36
article

Construction of planar chiral [2,2]paracyclophanes via photoinduced cobalt-catalyzed desymmetric addition

Ke Gao, Wenhan Xu, Liang‐Qiu Lu, Wei Xiong, Wen‐Jing Xiao, Xuan‐Feng Jiang, Ying Cheng, Zhihan Zhang, Huang Jiu-gui, Shiqi Liu
article en
10 citations

Abstract

Planar chiral [2,2]paracyclophanes (PCPs) are widely used in materials science and asymmetric syntheses. Therefore, synthetic and material chemists have focused on the efficient and selective construction of planar chiral PCPs for decades. Herein, we present a photoinduced cobalt-catalyzed desymmetric addition of pseudo-para-diformyl and pseudo-gem-diformyl PCP, enabling the synthesis of planar chiral PCP alcohols with both planar and central chiralities. This method delivers 48 examples with yields up to 87%, diastereomeric ratios greater than 19:1, and an enantiomeric excess exceeding 99%. This protocol provides a original and efficient approach for the synthesis of planar chiral PCPs.

Nature CommunicationsVol. 16(1)
Central China Normal University (CN), Lanzhou Institute of Chemical Physics (CN), Henan Normal University (CN), Lanzhou University (CN), Wuhan Institute of Technology (CN)
National Natural Science Foundation of China, Central China Normal University, Project 211
Openalex Percentile: Top 2%
Synthesis and Properties of Aromatic Compounds
9.36
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