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

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


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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