Abstract

The H 2PtCl 6 catalysed hydrosilylation of the terpenes (+)-α-fenchene ( XI), (−)-2-methylene bornane ( XII), (+)-camphene ( XIII) and (−)-3-methylene fenchane ( XIV) using HSiMe 2Cl or HSiMeCl 2 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 HSiMe 2Cl or HSiMeCl 2 is accompanied by a clean rearrangement of the isocamphane skeleton into (+)-2-methylene bornane ( XII) prior to hydrosilylation.

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