Synthesis of Axially Chiral <i>N</i>-Arylpyrroles through the Enantioselective Annulation of Yne-Allylic Esters with a Cooperative Copper-Squaramide Catalysis
We present a strategy involving central-to-axial chirality conversion for the construction of axially chiral <i>N</i>-arylpyrroles via a cooperative copper-squaramide-catalyzed remote propargylic amination/ring closure/rearomatization cascade from yne-allylic esters. The reaction exhibits excellent chemical efficiency and enantioselectivity, involving good central-to-axial chirality conversion. The use of squaramide as cocatalyst is crucial for the success.
Authors
- Jianwei Sun (ORCID: https://orcid.org/0000-0002-2470-1077)
- Hai Huang (ORCID: https://orcid.org/0000-0002-9732-1454)
- Zhengyu Han (ORCID: https://orcid.org/0000-0001-8317-6439)
- Yuzhe Zhang (ORCID: https://orcid.org/0000-0002-3975-4665)
- Jixing Li (ORCID: https://orcid.org/0000-0001-7136-2234)
- Maoyan Liao
- Haihui Zhu
Institutions
- Hong Kong University of Science and Technology (HK)
- Catalytic Materials (United States) (US)
- Changzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-08
- DOI
- https://doi.org/10.1021/acs.orglett.5c00700
- Citations
- 8
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 7.49
Funders
- National Natural Science Foundation of China
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department