Regiodivergent Synthesis of Oxadiazocines via Dirhodium-Catalyzed Reactivity of Oxazolidines and alpha-Imino Carbenes

Using electron-rich or electron-poor N-substituted oxazolidines as substrates, selective formation of either nitrogen or oxygen ylides is possible in the presence of alpha-imino carbenes. As such, treatment of 5-membered oxazolidine precursors with N-sulfonyl-1,2,3-triazoles under dirhodium catalysis (2 mol%) afford the regiodivergent synthesis of either 8-membered 1,3,6- or 1,4,6-oxadiazocines upon the initial N- or O-reactivity with the carbene.

    Organizational unit
    Laboratory of Professor Jérôme Lacour
    Type
    Dataset
    DOI
    10.26037/yareta:3cndx4brorddfaq4rc3oq2ggke
    Type
    Dataset
    License
    Creative Commons Attribution 4.0 International
Publication date10/02/2023
Retention date06/05/2033
accessLevelPublicAccess levelPublic
SensitivityBlue
duaNoneContract on the use of data
Contributors
  • Viudes, Olivier
  • Guarnieri-Ibáñez, Alejandro
  • Besnard, Céline orcid
  • Lacour, Jérôme orcid
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