Divergent synthesis of α-functionalized amides through selective N–O/C–C or N–O/C–C/C–N cleavage of aza-cyclobutanone oxime esters. Issue 75 (1st September 2021)

• Record Type: Journal Article
• Authors: Liu, Hua-Wei; Wang, Dian-Liang; Jiang, Nan-Quan; Li, Hai-Yan; Cai, Zhong-Jian; Ji, Shun-Jun
• Is Part Of: Chemical communications. Volume 57:Issue 75(2021)
• Page Start: 9618
• Page End: 9621
• Publication Date: 2021-09-01
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc03348d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A novel selective N–O/C–C or N–O/C–C/C–N cleavage of aza-cyclobutanone oxime esters is described. Abstract : 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.