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

ORGN 396

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Denise M. Elizondo, Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541.
A highly regioselective synthesis of gem-dimetalloalkanes containing silicon and aluminum 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 protonolysis of the resulting intermediates with water at 0oC provides the corresponding trimethylalkylsilanes in excellent yields (84%-92%). The structures of these trimethylalkylsilanes are confirmed by PMR and CMR spectral data.

 

Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005