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.
Authors
- Pierre H. Dixneuf (ORCID: https://orcid.org/0000-0002-3025-6969)
- Huanfeng Jiang (ORCID: https://orcid.org/0000-0002-4355-0294)
- Chengshuo Shen (ORCID: https://orcid.org/0000-0003-2422-3922)
- Min Zhang (ORCID: https://orcid.org/0000-0002-7023-8781)
- Zuyu Liang
- Yijian Ma
Institutions
- 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)
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
- Field-Weighted Citation Impact
- 0.00