Synthesis 2023; 55(20): 3393-3401
DOI: 10.1055/a-2096-4223
paper

Copper-Catalyzed Coupling of N-Phenoxyacetamides and 2H-Azirines for Synthesis of α-Amino Oxime Ethers

Authors

  • Yue-Lu Zhu

    a   School of Chemistry and Chemical Engineering, Heze University, Heze, 274015, Shandong, P. R. China
  • Jie Yan

    a   School of Chemistry and Chemical Engineering, Heze University, Heze, 274015, Shandong, P. R. China
  • Xiu-Xuan Xu

    a   School of Chemistry and Chemical Engineering, Heze University, Heze, 274015, Shandong, P. R. China
  • Zong-Yu Sun

    a   School of Chemistry and Chemical Engineering, Heze University, Heze, 274015, Shandong, P. R. China
  • Jiao Chen

    b   College of Chemistry & Materials Science, Northwest University, Xi’an, 710127, Shaanxi, P. R. China
    c   The College of Life Sciences, Northwest University, Xi’an, 710069, Shaanxi, P. R. China

We thank the Shandong Provincial Natural Science Foundation (ZR2022QB219) and Heze University for financial support.


Graphical Abstract

Abstract

Copper-catalyzed coupling reaction involving N-phenoxyacetamides and 2H-azirines is described, in which N–O and C–N bonds are broken and restructured. This protocol provides an efficient strategy for the highly regioselective synthesis of racemic α-amino oxime ethers. In addition, this strategy can be used to modify natural products and is gram-scale compatible.

Supporting Information



Publication History

Received: 27 March 2023

Accepted after revision: 19 May 2023

Accepted Manuscript online:
19 May 2023

Article published online:
19 June 2023

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