Organocatalytic enantio- and diastereoselective conjugate addition to nitroolefins: when beta-ketoamides surpass beta-ketoesters - Aix-Marseille Université Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2014

Organocatalytic enantio- and diastereoselective conjugate addition to nitroolefins: when beta-ketoamides surpass beta-ketoesters

Haiying Du
  • Fonction : Auteur
Jean Rodriguez
  • Fonction : Auteur
Xavier Bugaut

Résumé

Our findings on the bifunctional squaramide-catalyzed enantioselective conjugate addition of β-ketoamides to nitroolefins are disclosed. It appears that simple acyclic methylene β-ketoamides, unlike the extensively studied β-ketoesters, afford the products in excellent diastereoselectivities, and maintain high yields and enantioselectivities. Moreover, competition and kinetic studies were conducted to rationalize the observed reactivity and selectivity. The high level of diastereocontrol, along with the amenability of the amide group to postfunctionalization, dramatically increase the synthetic usefulness of the transformation.

Domaines

Chimie organique

Dates et versions

hal-01066616 , version 1 (22-09-2014)

Identifiants

Citer

Haiying Du, Jean Rodriguez, Xavier Bugaut, Thierry Constantieux. Organocatalytic enantio- and diastereoselective conjugate addition to nitroolefins: when beta-ketoamides surpass beta-ketoesters. Chemistry - A European Journal, 2014, pp.8458-8466. ⟨10.1002/chem.201402192⟩. ⟨hal-01066616⟩
16 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More