Remote Enantioselective Redox ε‐Alkylation of Copper Allylic Allenylidenes with Enals
The development of asymmetric functionalization at positions distant from the catalytic center-achieving high complexity, diversity, and stereocontrol-poses significant challenges. Here, we introduce an N-heterocyclic carbene (NHC)/copper cooperative catalytic strategy for the regioselective remote ε-alkylation of yne-allylic esters and yne-heteroarenic esters with enals, producing a diverse array of oxindoles with outstanding stereoselectivity (up to >95:5 dr, 99% ee). Remarkably, copper allylic allenylidenes are proven to be compatible with NHC-bound intermediates, facilitating efficient, regioselective, and stereoselective intermolecular C─C bond formation at distant sites.
Authors
- Shuai Li (ORCID: https://orcid.org/0000-0003-1977-2337)
- Yulin Lam (ORCID: https://orcid.org/0000-0003-0984-9492)
- Elvis Wang Hei Ng (ORCID: https://orcid.org/0000-0001-7189-8717)
- Liu‐Zhu Gong (ORCID: https://orcid.org/0000-0001-6099-827X)
- Qian‐Wei Gong
- Jin Song
Institutions
- University of Science and Technology of China (CN)
- Anhui University (CN)
- Hefei Institutes of Physical Science (CN)
- Hefei National Center for Physical Sciences at Nanoscale (CN)
- University of Hong Kong (HK)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2025-10-18
- DOI
- https://doi.org/10.1002/anie.202519335
- Citations
- 1
- Primary Topic
- N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.94