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Lewis acid- and Bronsted acid-catalyzed stereoselective rearrangement of epoxides derived from himachalenes: access to new chiral polycyclic structures |
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| Authors: | Abderrahim El Haib Ahmed Benharref Eric Manoury Martine Urrutigoïty Maryse Gouygou |
| Institution: | a CNRS, LCC (Laboratoire de Chimie de Coordination), 205, route de Narbonne, F-31077 Toulouse, France b Université de Toulouse, UPS, INPT, LCC, F-31077 Toulouse, France c Laboratoire de Chimie des substances naturelles Faculté des Sciences Semlalia, Université Cadi Ayyad, B.P. 2390 Marrakech, Morocco |
| Abstract: | The acid-catalyzed rearrangement of two enantiomerically pure epoxides derived from sesquiterpernic himachalenes, which are the main components of the essential oil of the Atlas cedar, has been studied using various Lewis and Bronsted acids. Several new polycyclic compounds have been obtained with different selectivities depending upon the catalysts used and the reaction conditions, and were fully characterized by spectroscopic methods. Mechanisms to explain the formation of the different compounds observed in the reaction mixture have also been proposed. |
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