Dataset for Polycyclic Pyrazolidines by Tandem Diazomalonate Dipolar Cycloadditions and CpRu-Catalyzed Carbene Additions

Thanks to the ability of diazo derivatives to react either as 1,3-dipoles and as carbenes after dinitrogen extrusion, combinations of oxa or aza benzonorbornadienes and diazomalonates afford polycyclic pyrazolidines via a three-step sequence of (i) a highly diastereoselective [3+2]-cycloaddition, (ii) a CpRu-catalyzed carbene addition, and (iii) a second dipolar cycloaddition. Of importance, step (II) represents a unique access to novel bench-stable N,N-cyclic azomethine imines, which behave as effective 1,3-dipoles in combination with electron-poor dipolarophiles. Each step proceeds efficiently and the 3-step process can be performed in one-pot to yield a polycyclic pyrazolidine in excellent overall yield (90%).

    Organizational unit
    Laboratory of Professor Jérôme Lacour
    Creative Commons Attribution 4.0 International
    Diazo compounds , Cycloaddition , Carbenes , Ylides , Ruthenium
Publication date16/04/2024
Retention date14/04/2034
accessLevelPublicAccess levelPublic
licenseContract on the use of data
  • Montagnon, Claire
  • Bultel, Joël
  • Besnard, Céline orcid
  • Guénée, Laure
  • Lacour, Jérôme orcid
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