Novel route to (Z)-allylsilanes containing trimethylsilylmethyl moiety via organoboranes

ORGN 630

Narayan G. Bhat, nbhat@panam.edu and Jessica I. Lopez. Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541
(E)-1-Trimethylsilylmethyl-1-alkenylboronate esters easily prepared by reacting ( Z)-bromo-1-alkenylboronate esters with trimethylsilylmethyllithium, readily react with alkyl or aryllithium in ether at -78 oC for 2 h. The resulting products are then treated with iodine in methanol at -78 oC for 3 h to provide after workup the corresponding ( Z)-allylsilanes containing trimethylsilylmethyl moiety in good yields (66%-80%) These ( Z)-allylsilanes containing trimethylsilylmethyl moiety are purified by column chromatography over alumina and the structures of these compounds are confirmed by NMR spectral data.