Highly Enantioselective Aza-Diels–Alder Reaction of 1-Azadienes with Enecarbamates Catalyzed by Chiral Phosphoric Acids


  • We wish to thank the ICSN and CNRS for financial support and Pascal Retailleau in ICSN for the X-ray crystallographic analysis. H.L. also acknowledges ANR for post-doctoral fellowships. G.L. thanks Diverchim for a CIFRE grant.


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On demand: A highly enantio- and diastereoselective synthesis of 6-amino- trisubstituted tetrahydropyridine compounds has been developed through the inverse-electron-demand aza-Diels–Alder reaction of N-aryl α,β-unsaturated ketimines with enecarbamates (E)-1. Chiral phosphoric acid catalysts achieve simultaneous activation of both the 1-azadiene and dienophile partners.