Asymmetric hydrosilylation of prochiral ketones in the presence of N-benzyl-N-methylephedrinium halometallates

N-benzyl-N-methylephedrinium hexachloroplatinate(IV), bromotrichlororhodate(III), and dibromodichlorozincate(II) have been synthesized by reacting (—)-N-benzyl-N-methylephedrinium bromide with K2PtCl6, RhCl3 · 4H2O and ZnCl2, respectively. The above halometallates have been found to catalyse the asymmetric hydrosilylation of acetophenone and 3-acetylpyridine with diphenylsilane. The hydrosilylation of 3-acetylpyridine in the presence of (—)-N-benzyl-N-methylephedrinium zincate followed by silyl ether hydrolysis gives 1-(3-pyridyl)ethanol in ca 50% optical yield.