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Copper(I)-catalyzed asymmetric decarboxylative Mannich reaction enabled by acidic activation of 2H-azirines

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  • Hai-Jun Zhang

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Yan-Cheng Xie

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Liang Yin

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

Abstract

Chiral aziridines are structure units found in many biologically active compounds and are important building blocks in organic synthesis. Herein, by merging nucleophilic generation through copper(I)-catalyzed decarboxylation and activation of poorly electrophilic 2H-azirines through protonation with carboxylic acids, an asymmetric decarboxylative Mannich reaction between α,α-disubstituted cyanoacetic acids and 2H-azirines is uncovered, which leads to generation of chiral aziridines containing vicinal tetrasubstituted and acyclic quaternary stereogenic carbon centers in good to excellent diastereo- and enantioselectivities. At last, transformations of the produced chiral aziridine are successfully carried out to deliver synthetically useful compounds.

Suggested Citation

  • Hai-Jun Zhang & Yan-Cheng Xie & Liang Yin, 2019. "Copper(I)-catalyzed asymmetric decarboxylative Mannich reaction enabled by acidic activation of 2H-azirines," Nature Communications, Nature, vol. 10(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-09750-5
    DOI: 10.1038/s41467-019-09750-5
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