Molecular rearrangement of epoxide derived from sesquiterpenes by Lewis acid catalysis

The molecular rearrangement under mild conditions of two epoxides derived from the sesquiterpenic himachalenes has been studied using BF 3·Et 2O as the Lewis acid catalyst. Both reactions are efficient and selective affording in each case one new enantiomerically pure ketone isolated in good yield....

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2010-05, Vol.21 (9), p.1272-1277
Main Authors: Haib, Abderrahim El, Benharref, Ahmed, Parrès-Maynadié, Sandra, Manoury, Eric, Daran, Jean-Claude, Urrutigoïty, Martine, Gouygou, Maryse
Format: Article
Language:English
Subjects:
Analytical chemistry
Chemical Sciences
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Summary:The molecular rearrangement under mild conditions of two epoxides derived from the sesquiterpenic himachalenes has been studied using BF 3·Et 2O 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 BF 3-catalyzed reactions are proposed.
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/j.tetasy.2010.04.024