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Access to Highly Functionalized Sulfonated Cyclopentanes by Acid‐Promoted Rauhut–Currier Reaction with Sulfinamides |
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| Authors: | Dr. Nicolas Gigant Dr. Emmanuelle Drège Dr. Pascal Retailleau Prof. Delphine Joseph |
| Affiliation: | 1. Université Paris‐Sud, UMR CNRS 8076 BioCIS, LabEx Lermit, Equipe de Chimie des Substances Naturelles, 5, rue Jean‐Baptiste Clément, 92296 Chatenay‐Malabry (France);2. Institut de Chimie des Substances Naturelles, UPR CNRS 2301, Bat. 27, 1, Avenue de la Terrasse, 91198 Gif‐sur‐Yvette cedex (France), Orgdiv |
| Abstract: | 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. |
| Keywords: | carbocycles cascade reactions cycloisomerization Michael addition sulfinamides |