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

Hai-Jun Zhang, Yan-Cheng Xie and Liang Yin ()
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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

Nature Communications, 2019, vol. 10, issue 1, 1-8

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-019-09750-5

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