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.

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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
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article

Remote Enantioselective Redox ε‐Alkylation of Copper Allylic Allenylidenes with Enals

Shuai Li, Yulin Lam, Elvis Wang Hei Ng, Liu‐Zhu Gong et al.
1 citations
Angewandte Chemie International Edition
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
0.94
article

Remote Enantioselective Redox ε‐Alkylation of Copper Allylic Allenylidenes with Enals

Shuai Li, Yulin Lam, Elvis Wang Hei Ng, Liu‐Zhu Gong, Qian‐Wei Gong, Jin Song
article en
1 citations

Abstract

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.

Angewandte Chemie International EditionVol. 64(51)
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)
Openalex Percentile: Top 20%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
0.94
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