Cobalt-Catalyzed Asymmetric Reductive Propargylic Addition of α-Ketimino Esters

The Nozaki-Hiyama-Kishi (NHK) reaction serves as a powerful method for stereoselective carbon-carbon bond formation under mild conditions. While significant progress has been made in the enantioselective propargylation of carbonyl compounds, its application to imines remains underdeveloped. Herein, we report a catalytic asymmetric reductive propargylic addition to α-ketimino esters, providing direct access to chiral propargylated amines with high chemoselectivity and enantioselectivity. This method expands the synthetic utility of NHK-type reactions toward nitrogen-containing scaffolds, offering a complementary route to enantioenriched amine derivatives under mild and efficient conditions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-02-06
DOI
https://doi.org/10.1021/acs.joc.5c02793
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
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article

Cobalt-Catalyzed Asymmetric Reductive Propargylic Addition of α-Ketimino Esters

Ning Liu, Yuehua Chen, Wenyu Zhao, Jingping Qu et al.
The Journal of Organic Chemistry
Asymmetric Hydrogenation and Catalysis
article

Cobalt-Catalyzed Asymmetric Reductive Propargylic Addition of α-Ketimino Esters

Ning Liu, Yuehua Chen, Wenyu Zhao, Jingping Qu, Wei-Hong Zhu, Xianqing Wu, Zhiying Yu
article en

Abstract

The Nozaki-Hiyama-Kishi (NHK) reaction serves as a powerful method for stereoselective carbon-carbon bond formation under mild conditions. While significant progress has been made in the enantioselective propargylation of carbonyl compounds, its application to imines remains underdeveloped. Herein, we report a catalytic asymmetric reductive propargylic addition to α-ketimino esters, providing direct access to chiral propargylated amines with high chemoselectivity and enantioselectivity. This method expands the synthetic utility of NHK-type reactions toward nitrogen-containing scaffolds, offering a complementary route to enantioenriched amine derivatives under mild and efficient conditions.

The Journal of Organic ChemistryVol. 91(7)
East China University of Science and Technology (CN)
Openalex Percentile: Top 66%
Asymmetric Hydrogenation and Catalysis
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