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February 8, 20260 citations

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

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NLNing LiuZYZhiying YuWZWenyu Zhao

Key Points

  • The aim is to develop a stereoselective method for the propargylic addition to α-ketimino esters.
  • Utilized the Nozaki-Hiyama-Kishi reaction for carbon-carbon bond formation.
  • Implemented cobalt-catalyzed asymmetric reductive addition.
  • Targeted α-ketimino esters to synthesize chiral propargylated amines.
  • Achieved high enantioselectivity and chemoselectivity in product formation.
  • Provided a complementary synthetic route for nitrogen-containing compounds.

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.

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Cite This Study

Liu et al. (2026) studied this question.

synapsesocial.com/papers/698828b90fc35cd7a88486dehttps://doi.org/10.1021/acs.joc.5c02793
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