Asymmetric Intramolecular Hydroamination to Construct Diverse N–N/C–N Indole Atropisomers via Cooperative Pd(0) and Chiral Phosphoric Acid Catalysis
Here we present an enantioselective intramolecular hydroamination reaction of <i>o</i>-aminophenyl-1,3-enynes via cooperative catalysis of Pd(0) and chiral phosphoric acid. This approach enables the efficient construction of N-N/C-N axially stereogenic indoles with broad skeletal diversity and high levels of enantioselectivity in a completely atom-economic manner. Mechanistic studies indicate that a protonation of the alkyne moiety via Pd(0) π-Lewis base activation is favored, and the chiral phosphate counteranion plays a crucial role in controlling the atroposelectivity in the ring-closure step.
Authors
- Wei Du (ORCID: https://orcid.org/0000-0003-4162-1471)
- Qin Ouyang (ORCID: https://orcid.org/0000-0002-1161-5102)
- Shun‐Zhong Tan
- Fu Pi
- Xiaojun Wang (ORCID: https://orcid.org/0000-0001-8049-5020)
- Zhi Chen (ORCID: https://orcid.org/0000-0002-4032-5120)
- Ying‐Chun Chen (ORCID: https://orcid.org/0000-0003-1902-0979)
- Yufan Li (ORCID: https://orcid.org/0000-0001-8191-2738)
- Lei Zhu (ORCID: https://orcid.org/0000-0002-7870-8469)
Institutions
- Army Medical University (CN)
- Sichuan University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c00662
- Citations
- 6
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 5.62
Funders
- National Natural Science Foundation of China
- National Key Research and Development Program of China