Novel route to (Z)-1-alkenylboronate esters via (Z)-1-trimethylstannyl-1-alkenes

ORGN 628

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Magaly Salinas, xaquis105@yahoo.com, Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541.
(Z)-1-Trimethylstannyl-1-alkenes easily prepared by the hydrozirconation of the corresponding 1-trimethylstannyl-1-alkynes followed by hydrolysis readily react with boron trichloride in hexanes for 4 h at room temperature. The resulting boron intermediates are then treated with water at 0 oC followed by extraction with ether. The resulting (Z)-1-alkenylboronic acids are then esterified with 1,3-propane diol in n-pentane for 1 h at room temperature. The (Z)-1-alkenylboronate esters are then isolated in good yieids (76%-85%) and their structures are confirmed by spectral (PMR and CMR) data.
 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008