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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.
- Source :
- Chemical Communications; 9/25/2021, Vol. 57 Issue 75, p9618-9621, 4p
- Publication Year :
- 2021
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- AMIDES
ESTERS
ISOCYANIDES
Subjects
Details
- Language :
- English
- ISSN :
- 13597345
- Volume :
- 57
- Issue :
- 75
- Database :
- Complementary Index
- Journal :
- Chemical Communications
- Publication Type :
- Academic Journal
- Accession number :
- 152553488
- Full Text :
- https://doi.org/10.1039/d1cc03348d