(Z)-1-Beomo-1-alkenylboronate esters easily prepared from literature procedures, readily react with trimethylsilylmethyllithium at lower temperature ti provide the corresponding "are" complexes. These "are" complexes readily undergo the migration of trimethylsilylmethyl group from boron to carbon providing (E)-trisubsrituted alkenes containing a trimethylsilylmethyl moiety..It was then subjected to a reaction with p-methoxyphenylmagnesium bromide followed by treatment with iodine in methanol. The resulting alkenes are isolated in 65%-82% yields. The products are purified by column chromarography over alumina and the structures are confirmed by NMR specreal dara.

New diastereoselective synthesis of (E)-trisubsritutrd alkenes containing trimethylsilylmethyl and p-methoxyphenyl moities via organoboranes

249th National Meeting (2015)

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