Activation of 1,2- and 1,3-Ketoamides with Thiourea Organocatalyst for the Enantioselective Domino Synthesis of Fuctionalized Cyclohexanes

Wilfried Raimondi (1) , Maria del Mar Sanchez Duque (1) , Sébastien Goudedranche (2) , Adrien Quintard (2) , Thierry Constantieux (1) , Xavier Bugaut (2) , Damien Bonne (1) , Jean Rodriguez (1)

1 STeRéO
2 ISM2 - Institut des Sciences Moléculaires de Marseille

Several reactive sites of 1,2- and 1,3-ketoamides were successively exploited in two complementary domino transformations for the synthesis of polysubstituted monocyclic or bridged bicyclic cyclohexanes, with the creation of up to six stereogenic centers. In both cases, a chiral bifunctional thiourea organocatalyst allowed efficient control of chirality in the final carbocycle.

Mots clés: domino reactions; ketones; amides; cyclizations; cycloalkanes; stereoselectivity; catalysis; thioureas

Domaines: Chimie organique

Wilfried Raimondi, Maria del Mar Sanchez Duque, Sébastien Goudedranche, Adrien Quintard, Thierry Constantieux, et al.. Activation of 1,2- and 1,3-Ketoamides with Thiourea Organocatalyst for the Enantioselective Domino Synthesis of Fuctionalized Cyclohexanes. Synthesis: Journal of Synthetic Organic Chemistry, 2013, 45, pp.1659-1666. ⟨10.1055/s-0033-1338844⟩. ⟨hal-00861637⟩