(Z)-1-Bromo 1-alkenylboronate esters easily prepared by the literature procedures, readily react with 2-naphthyllmagnesium bromide  in ether at -78 oC for 1 h to provide the corresponding �ate� complexes. These �ate� complexes  then undergo the migration of a p-methoxyphenyl group from boron to the adjacent carbon provoding (E)-trisubstituted alkenyl boronate esters containing a 2-naphthyl  moiety. These (E)-trisubstitutedalkenyl boronate esters are obtained  in 68%-80% isolated yields. They are then reacted with 4-biphenylmagnesium bromide followed by treatment with iodine in methanol  for 3 h providing the corresponding (Z)-trisubstituted alkenes containing a biphenyl moiety in 70%-82% isolated yields.  These products are then purified by column chromatography over  alumina  and the structures of these compounds are  confirmed by  NMR spectral data.

New diastereoselective synthesis of (Z)-trisubstituted alkenes containing a biphenyl and naphthyl moieties  via organoboranes

246th National Meeting (2013)

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