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Total diastereofacial selective iodofunctionalization of terpene derivatives based on Ipy2BF4
José Barluenga1, Mónica Alvarez-Pérez, Félix Rodríguez
1Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al C.S.I.C., Universidad de Oviedo, Julián Clavería, 8, E-33006, Oviedo, Spain. barluenga@sauron.quimica.uniovi.es
The Journal of Organic Chemistry
|August 16, 2003
Abstract:
Acetonides 1, easily obtained from simple terpenes, react with bispyridine iodonium (I) tetrafluoroborate (Ipy(2)BF(4)) and tetrafluoroboric acid in the presence of nucleophiles to give the corresponding adducts 2 with complete regio and diastereofacial control. Acetonides 1 containing a properly located phenyl or benzyloxy group easily undergo iodocyclization to furnish compounds 3 and 4.