Dataset of Regiodivergent Synthesis of Pyrazino-Indolines vs. Triazocines via α-Imino Carbenes Addition to Imidazolidines

Hexahydropyrazinoindoles were prepared in a single step from N-sulfonyl triazoles and imidazolidines. Under dirhodium catalysis, α-imino carbenes were generated and formed nitrogen ylide intermediates that, after subsequent aminal opening, afforded the pyrazinoindoles predominantly via formal [1,2]-Stevens and tandem Friedel-Crafts cyclizations. Of mechanistic importance, a regiodivergent reactivity was engineered through the use of a specific unsymmetrically substituted imidazolidine that promoted the exclusive formation of 8-membered ring 1,3,6-triazocines. Based on first principles, an original Curtin-Hammett-like situation was demonstrated for the mechanism. Further derivatizations lead to functionalized tetrahydropyrazinoindoles in high yields

    Organizational unit
    Laboratory of Professor Jérôme Lacour
    Type
    Dataset
    DOI
    10.26037/yareta:u5rrhkxqyrgbhpijt7uhyqi6eq
    License
    Creative Commons Attribution 4.0 International
Publication date15/10/2020
Retention date07/11/2030
accessLevelPublicAccess levelPublic
SensitivityUndefined
duaNoneContract on the use of data
Contributors
  • Guarnieri-Ibáñez, Alejandro
  • de Aguirre, Adiran
  • Besnard, Céline orcid
  • Poblador Bahamonde, Amalia orcid
  • Lacour, Jérôme orcid
13
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