Hydroalumination of (Z)-1-trimethylstannyl-1-alkenes followed by selective iodinolysis

ORGN 546

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Magaly Salinas, Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541.
A highly regioselective synthesis of 1-iodoalkyltrimethylstannanes is presented. (Z)-1-Trimethylstannyl-1-alkenes (easily prepared by the hydrozirconation of the corresponding 1-trimethylstannyl-1-alkynes followed by protonolysis) smoothly undergo hydroalumination with diisobutylaluminum hydride (DIBAL-H) in hexanes at room temperature for 16 h. The selective iodinolysis of the resulting intermediates with iodine at 0 oC for an hour provides the corresponding 1-iodoalkyltrimethylstannanes in good yields (70%-82%). The structures of these intermediates are confirmed by PMR and CMR spectral data.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007