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An unprecedented outcome of the lithium–ammonia reduction of enones: the formation of cyclopropanols |
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| Authors: | Fran oise Dumas, Cyrille Thominiaux, Christine Miet, Jean d'Angelo, Didier Desmaë le, Mohammed Nour, Christian Cav , Georges Morgant,Marie-Elise Tran Huu-Dau |
| Affiliation: | aUnité de Chimie Organique associée au CNRS, Université Paris-Sud, Centre d'Etudes Pharmaceutiques, 5 rue J.-B. Clément, 92296 Châtenay-Malabry, France bUnité de Molécules d'Intérêt Biologique, UFR Pharmacie, BP 87900, 21079 Dijon, France cLaboratoire de Cristallochimie Bioinorganique, Université Paris-Sud, Faculté de Pharmacie, 5 rue J.-B. Clément, 92296 Châtenay-Malabry, France dInstitut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif sur Yvette, France |
| Abstract: | An unusual process takes place during the lithium–ammonia reduction of a variety of cyclic enones bearing an ester group in the γ-position, furnishing cyclopropanols. The reason for this unprecedented outcome has been attributed to the through-space stabilization of a developing cyclopropyl radical by interaction with the neighboring ester substituent. |
| Keywords: | cyclopropanation enones reduction radical and radical reactions molecular modeling/mechanics |
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