Novel synthesis of (E)-allylsilanes via organoboranes

ORGN 169

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Wendy C. Lai, Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541.
(Z)-1-Alkenylboronate esters easily prepared by the hydroboration of 1-bromo-1-alkynes with dibromoborane-methyl sulfide complex and by the reaction with 1,3-propane diol followed by treatment with potassium triisopropoxyborohydride (KIPBH) readily react with trimethylsilylmethyllithium in ether at -78 oC for 2 h. The resulting product is then treated with iodine at -78 oC for 3 h to provide after workup the corresponding (E)-allylsilanes in good yields (72%-80%) These (E)-allylsilanes are purified by column chromatography over alumina and the structures of these compounds are confirmed by NMR spectral data.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006