684284-10-4Relevant articles and documents
Chiral organochlorosilanes derived from terpenes: Diastereoselective hydrosilylation of methylene bicyclo[2.2.1]heptanes with HSiMenCln-2 (n = 0-2)
Beckmann, Jens,Dakternieks, Dainis,Duthie, Andrew,Floate, Susan L.,Foitzik, Richard C.,Schiesser, Carl H.
, p. 909 - 916 (2007/10/03)
The H2PtCl6 catalysed hydrosilylation of the terpenes (+)-α-fenchene (XI), (-)-2-methylene bornane (XII), (+)-camphene (XIII) and (-)-3-methylene fenchane (XIV) using HSiMe2Cl or HSiMeCl2 proceeds with high regioselectively and in some cases, with high diastereoselectivity. KF-assisted oxidation of the hydrosilylation products gives predominately endo-terpene alcohols. The alcohols have inverted endo/exo ratios to those formed by oxidative hydroboration. Reaction of XIV with HSiMe2Cl or HSiMeCl2 is accompanied by a clean rearrangement of the isocamphane skeleton into (+)-2-methylene bornane (XII) prior to hydrosilylation.