Atroposelective Synthesis of Enamine‐Based Axially Chiral Styrenes via CuH‐Catalyzed Hydroamination of Internal Alkynes

Abstract Despite the significant potential of axially chiral enamines, their efficient synthesis remains a challenge. Herein, we report a new approach for the diverse synthesis of enamine‐based axially chiral styrenes via a copper‐catalyzed atroposelective hydroamination of internal alkynes. This method features good functional group tolerance, exclusive regio‐ and E ‐selectivity, and excellent enantioselectivities (up to 98% ee). Experimental and DFT studies were performed to elucidate the mechanism and rationalize the origin of enantioselectivity. Furthermore, the reaction is readily scalable to gram quantities, and the resulting products can be transformed into chiral N,P‐ligands, thereby enriching the family of axially chiral ligands with new members.

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Publication Details

Journal
Angewandte Chemie
Published
2025-09-20
DOI
https://doi.org/10.1002/ange.202516510
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
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article

Atroposelective Synthesis of Enamine‐Based Axially Chiral Styrenes via CuH‐Catalyzed Hydroamination of Internal Alkynes

Pierre H. Dixneuf, Huanfeng Jiang, Chengshuo Shen, Min Zhang et al.
Angewandte Chemie
Axial and Atropisomeric Chirality Synthesis
article

Atroposelective Synthesis of Enamine‐Based Axially Chiral Styrenes via CuH‐Catalyzed Hydroamination of Internal Alkynes

Pierre H. Dixneuf, Huanfeng Jiang, Chengshuo Shen, Min Zhang, Zuyu Liang, Yijian Ma
article en

Abstract

Abstract Despite the significant potential of axially chiral enamines, their efficient synthesis remains a challenge. Herein, we report a new approach for the diverse synthesis of enamine‐based axially chiral styrenes via a copper‐catalyzed atroposelective hydroamination of internal alkynes. This method features good functional group tolerance, exclusive regio‐ and E ‐selectivity, and excellent enantioselectivities (up to 98% ee). Experimental and DFT studies were performed to elucidate the mechanism and rationalize the origin of enantioselectivity. Furthermore, the reaction is readily scalable to gram quantities, and the resulting products can be transformed into chiral N,P‐ligands, thereby enriching the family of axially chiral ligands with new members.

Angewandte ChemieVol. 137(46)
Centre National de la Recherche Scientifique (FR), Zhejiang Sci-Tech University (CN), Université Rennes 2 (FR), Zero to Three (US), Université de Rennes (FR), South China University of Technology (CN)
Openalex Percentile: Top 81%
Axial and Atropisomeric Chirality Synthesis
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Atroposelective Synthesis of Enamine‐Based Axially Chiral Styrenes via CuH‐Catalyzed Hydroamination of Internal Alkynes — Pierre H. Dixneuf, Huanfeng Jiang, et al. · Angewandte Chemie (2025) | TGRS Research Map | TGRS