Divergent synthesis of a-functionalized amides through selective N–O/C–C or N–O/C–C/C–N cleavage of aza-cyclobutanone oxime esters
Hua-Wei Liu a, Dian-Liang Wang a, Nan-Quan Jiang a, Hai-Yan Li b, Zhong-Jian Cai *a（蔡忠建） and Shun-Jun Ji *a（纪顺俊）
a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou, 215123, P. R. China.
b Analysis and Testing Center, Soochow University, Suzhou 215123, China
Chem. Commun., 2021, 57, 9618--9621
Herein, a novel sequential ring opening reaction of aza-cyclobutanone oxime esters with isocyanides is described. The reaction proceeded smoothly under redox-neutral and mild conditions, leading to a divergent synthesis of α-cyanomethylaminoamides, α-acyloxyamides and α-acylaminoamides. In these transformations, a selective N–O/C–C or N–O/C–C/C–N cleavage was achieved only by changing the iron-catalyst system. Among them, a rare sequential N–O/C–C/C–N cleavage process with a classical Passerini or Ugi multicomponent reaction can be executed in a single step. To the best of our knowledge, this work creates a novel reaction mode of cycloketone oximes and provides new opportunities for reaction design.
链接：//pubs.rsc.org/en/content/articlelanding/2021/cc/d1cc03348d
