Regioselective methylation of the secondary carbinol center of prim, sec-diols

Article abstract of DOI:10.1016/S0040-4039(98)00445-6

Reaction of 2-oxo-4-phenyl-1,3,2-dioxathiolane and 2-oxo-4-(tert- butyldiphenylsilylmethyl)-13,2-dioxathiolane with trimethylaluminium selectively took place at the secondary carbinol center to give 2-phenyl-1- propanol and 3-(tert-butyldiphenylsilyl)-2-methylpropanol. When the endo- or exo-isomer of (S)-2-oxo-4-phenyl-13,2-dioxathiolane reacted with trimethylaluminium, (R)-2-phenyl-1-propanol was obtained in 75% ee or 90% ee, respectively.