Highly Enantioselective Aza-Diels–Alder Reaction of 1-Azadienes with Enecarbamates Catalyzed by Chiral Phosphoric Acids†
Dr. Long He
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)
Search for more papers by this authorGregory Laurent
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)
Search for more papers by this authorDr. Pascal Retailleau
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)
Search for more papers by this authorDr. Benoît Folléas
Diverchim, ZAC du Moulin, 6 rue du Noyer, 95700 Roissy-en-France (France)
Search for more papers by this authorDr. Jean-Louis Brayer
Diverchim, ZAC du Moulin, 6 rue du Noyer, 95700 Roissy-en-France (France)
Search for more papers by this authorCorresponding Author
Dr. Géraldine Masson
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)Search for more papers by this authorDr. Long He
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)
Search for more papers by this authorGregory Laurent
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)
Search for more papers by this authorDr. Pascal Retailleau
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)
Search for more papers by this authorDr. Benoît Folléas
Diverchim, ZAC du Moulin, 6 rue du Noyer, 95700 Roissy-en-France (France)
Search for more papers by this authorDr. Jean-Louis Brayer
Diverchim, ZAC du Moulin, 6 rue du Noyer, 95700 Roissy-en-France (France)
Search for more papers by this authorCorresponding Author
Dr. Géraldine Masson
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex (France)Search for more papers by this authorWe 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.
Graphical Abstract
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.
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