Novel synthesis of (Z)-allylsilanes containing trimethylsilylmethyl moiety via organoboranes

ORGN 547

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-Alkyl-1-alkenylboronate esters easily prepared by the literature procedures, readily react with trimethylsilylmethyllithium in ether at -78 oC for 2 h. The resulting products are then treated with iodine at -78 oC for 3 h to provide after workup the corresponding (Z)-allylsilanes containing trimethylsilylmethyl moiety in good yields (68%-78%) 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.