Total diastereofacial selective iodofunctionalization of terpene derivatives based on Ipy2BF4.
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.
Barluenga
José
J
Instituto 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
Alvarez-Pérez
Mónica
M
Rodríguez
Félix
F
Fañanás
Fracisco J
FJ
Cuesta
José A
JA
García-Granda
Santiago
S
D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
D011725:Pyridines; D013729:Terpenes