The (Z)-1-alkenyboronate esters easily prepared by the reaction of (Z)-1-bromoalkenylboronate esters with potassium triisopropoxy borohydride (KIPBH), readily react with p-methoxyphenyl magnesium bromide in ether at -78 oC for 1 hour to provide the corresponding 'ate' complexes. These 'ate' complexes in methanol are then treated with iodine in methanol at -78 oC for 3 hours provide the corresponding (E)-disubstituted alkenes containing a p-methoxyphenyl moiety. These products are then purified by column chromatography over alumina and the structures of these compounds are confirmed by NMR spectral data. These compounds are obtained in good yields (65%-78%).

Highly diastereoselective synthesis of (<i>E</i>)-disubstituted alkenes containing a <i>p</i>-methoxyphenyl moiety via organoboranes

243rd National Meeting (2012)

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Highly diastereoselective synthesis of (E)-disubstituted alkenes containing a p-methoxyphenyl moiety via organoboranes