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Free-radical functionalisation of vinylcyclopropanes |
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| Authors: | Olivier AndreyBoris Camuzat-Dedenis Laurent ChabaudKarine Julienne Yannick Landais Liliana Parra-RapadoPhilippe Renaud |
| Affiliation: | a Laboratoire de Chimie Organique et Organométallique, University Bordeaux-1, 351, Cours de la Libération, 33405 Talence cedex, France b Departement für Chemie und Biochemie, Freiestrasse 3, 3000 Bern 9, Switzerland |
| Abstract: | Free-radical mediated cyclopropane ring opening of 2-silylbicyclo[3.1.0]hexane 1 has been carried out leading to the corresponding trisubstituted cyclopentenes 5 and 6 in good yield with complete 1,2-stereocontrol. [3+2]-Annulation has also been performed by trapping the resulting radical with electron-rich and electron-poor olefins, leading to the corresponding polycyclic compounds. Further studies on the functionalisation of dihydropyridines and pyrroles using this methodology is also described. |
| Keywords: | radicals cyclopropanes silicon and compounds selenium and compounds annulation allylsilanes |
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