Organocatalytic enantio- and diastereoselective conjugate addition to nitroolefins: when beta-ketoamides surpass beta-ketoesters - Aix-Marseille Université Access content directly
Journal Articles Chemistry - A European Journal Year : 2014

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

Haiying Du
  • Function : Author
Jean Rodriguez
  • Function : Author
Xavier Bugaut

Abstract

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.

Dates and versions

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

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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⟩
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