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1,3-DC reactions of ketonitrones

1,3-DC reactions of ketonitrones

We have extensively study the 1,3-DC reactions of new dipoles : the carboxy ketonitrones with a range of ethylenic dipolarophiles, with emphasis on the scope of the catalytic asymmetric reaction leading in a highly stereocontrolled manner to valuable multifunctional adducts, containing one or two quaternary centers.

In several cases, our dual experimental / computional study gave new insights on the mechanisms of such catalytic asymmetric 1,3-DC reactions.



  • Mathieu Laurent
  • Arnaud Martel
  • Gilles Dujardin

Related papers

  • Cationic Ru-catalyzed of 1,3-DC reactions of carboxy Ketonitrones with metacroleïne: Selim, K.B.; Martel, A.; Laurent, M. Y.; Lhoste, J. ; Py, S.; Dujardin, G. J. Org. Chem. 2014, 79, 3414.
  • Iminium-based catalyzed 1,3-DC reactions of carboxy Ketonitrones with crotonaldehyde: Ben Ayed, K. Laurent, M. Y.; Martel, A.; Selim, K. B.; Abid, S.; A.; Dujardin, G. Eur. J. Org. Chem. 2017, 79, 6763.
  • Review on Isozaolidines (Synthesis and uses in medicinal chemistry): M. Berthet, T. Cheviet, G. Dujardin, I. Parrot, J. Martinez, Chem. Rev. 2016, 116, 15235.
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