Iron-Catalyzed Asymmetric Cross-Electrophile Alkylation of Imines

Transition metal-catalyzed asymmetric cross-electrophile coupling has emerged as a synthetically useful strategy for the stereoselective construction of a carbon–carbon bond. Herein, we report an iron-catalyzed enantioselective cross-electrophile alkylation of α-imino esters with unactivated alkyl halides by employing a chiral NPN ligand. This method delivers α-tetrasubstituted amino esters in high yields (up to 93%) and enantioselectivity (up to 97:3 er), accommodating diverse substrates, including primary, secondary, and tertiary alkyl iodides, with broad functional group tolerance. The system is extended to asymmetric benzylation using benzyl chlorides, yielding chiral phenylalanine derivatives bearing quaternary stereocenters (up to 97.5:2.5 er), including bioactive motifs. Mechanistic studies suggest alkyl radical intermediates and a low-valent iron catalytic cycle initiated by a single-electron transfer.

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Publication Details

Journal
ACS Catalysis
Published
2025-08-15
DOI
https://doi.org/10.1021/acscatal.5c04547
Citations
9
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
8.42

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article

Iron-Catalyzed Asymmetric Cross-Electrophile Alkylation of Imines

Jingping Qü, Xianqing Wu, Yiwen Shen, Qinglin Wang et al.
9 citations
ACS Catalysis
Catalytic C–H Functionalization Methods
8.42
article

Iron-Catalyzed Asymmetric Cross-Electrophile Alkylation of Imines

Jingping Qü, Xianqing Wu, Yiwen Shen, Qinglin Wang, Yifeng Chen, Wenyu Zhao, Jiahao Bai, Yuquan Xin
article en
9 citations

Abstract

Transition metal-catalyzed asymmetric cross-electrophile coupling has emerged as a synthetically useful strategy for the stereoselective construction of a carbon–carbon bond. Herein, we report an iron-catalyzed enantioselective cross-electrophile alkylation of α-imino esters with unactivated alkyl halides by employing a chiral NPN ligand. This method delivers α-tetrasubstituted amino esters in high yields (up to 93%) and enantioselectivity (up to 97:3 er), accommodating diverse substrates, including primary, secondary, and tertiary alkyl iodides, with broad functional group tolerance. The system is extended to asymmetric benzylation using benzyl chlorides, yielding chiral phenylalanine derivatives bearing quaternary stereocenters (up to 97.5:2.5 er), including bioactive motifs. Mechanistic studies suggest alkyl radical intermediates and a low-valent iron catalytic cycle initiated by a single-electron transfer.

ACS CatalysisVol. 15(17)
East China University of Science and Technology (CN), Chinese Academy of Sciences (CN), Shanghai Institute of Organic Chemistry (CN), State Key Laboratory of Organometallic Chemistry, Henan Normal University (CN)
National Natural Science Foundation of China, Science and Technology Commission of Shanghai Municipality, China Petrochemical Corporation, Higher Education Discipline Innovation Project, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 2%
Catalytic C–H Functionalization Methods
8.42
DOISourceOpenAlex
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Iron-Catalyzed Asymmetric Cross-Electrophile Alkylation of Imines — Jingping Qü, Xianqing Wu, et al. · ACS Catalysis (2025) | TGRS Research Map | TGRS