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Molecular rearrangement of epoxide derived from sesquiterpenes by Lewis acid catalysis |
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| Authors: | Abderrahim El Haib Ahmed Benharref Sandra Parrès-Maynadié Eric Manoury Jean-Claude Daran Martine Urrutigoïty Maryse Gouygou |
| Affiliation: | 1. CNRS, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, F-31077 Toulouse, France;2. Université de Toulouse, UPS, INPT, LCC, F-31077 Toulouse, France;3. Laboratoire de Chimie des substances naturelles, Faculté des Sciences Semlalia, Université Cadi Ayyad, B.P. 2390, Marrakech, Morocco |
| Abstract: | The molecular rearrangement under mild conditions of two epoxides derived from the sesquiterpenic himachalenes has been studied using BF3·Et2O as the Lewis acid catalyst. Both reactions are efficient and selective affording in each case one new enantiomerically pure ketone isolated in good yield. Their structures have been fully characterized by spectroscopic methods. Mechanisms for the BF3-catalyzed reactions are proposed. |
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