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

ORGN 170

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-iodoalkyltrimethylsilanes is presented. (Z)-Trimethylsilyl-1-alkenes (easily prepared by the hydrozirconation of the corresponding 1-trimethylsilyl-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-iodoalkyltrimethylsilanes in high yields (76%-88%). The structures of these intermediates are confirmed by PMR and CMR 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