A catalytic, asymmetric allylation reaction of aldehydes or ketones with allyltrimethoxysilane was achieved by using a BINAP·AgBF4 [BINAP = 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl] complex as the chiral precatalyst and triethylamine as the base precatalyst in the presence of 2,2,2‐trifluoroethanol. Optically active homoallylic alcohols with up to 95 % ee were obtained in moderate to high yields through the in situ generated chiral allyl silver catalyst.
A catalytic asymmetric addition of propargylic silanes to aldehydes was achieved using a DM-BINAP⋅AgBF 4 complex as the chiral pre-catalyst and triethylamine as the base precatalyst in the presence of potassium fluoride and methanol. Optically active homoallenylic alcohols and homopropargylic alcohols were obtained in moderate to high combined yields via the in situ generated chiral organosilver species. Allenylated alcohols were formed predominantly with up to 95% ee.
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