Access to Highly Functionalized Sulfonated Cyclopentanes by Acid-Promoted Rauhut-Currier Reaction with Sulfinamides.
An unexpected acid-mediated cascade reaction induced by conjugate addition of sulfinamides to dienediones has been developed. This highly efficient Rauhut-Currier reaction enables the rapid, high-yielding construction of sulfonated cyclopentanes with three contiguous stereogenic centers in a single operation starting from simple sulfinamides. This process constitutes the first example of sulfinamide-promoted cycloisomerization.
Université Paris-Sud, UMR CNRS 8076 BioCIS, LabEx Lermit, Equipe de Chimie des Substances Naturelles, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry (France).
Nicolas
N
Gigant
Université Paris-Sud, UMR CNRS 8076 BioCIS, LabEx Lermit, Equipe de Chimie des Substances Naturelles, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry (France).
Emmanuelle
E
Drège
Institut de Chimie des Substances Naturelles, UPR CNRS 2301, Bât. 27, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette cedex (France), Orgdiv.
Pascal
P
Retailleau
Université Paris-Sud, UMR CNRS 8076 BioCIS, LabEx Lermit, Equipe de Chimie des Substances Naturelles, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry (France). delphine.joseph@u-psud.fr.
Delphine
D
Joseph
Michael addition; carbocycles; cascade reactions; cycloisomerization; sulfinamides