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

ORGN 171

Narayan G. Bhat, nbhat@panam.edu, Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 and Ricardo Medina Jr., Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541.
A highly regioselective synthesis of gem-dimetalloalkanes containing tin and aluminum 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 protonolysis of the resulting intermediates with water at 0 oC provides the corresponding trimethylalkylstannanes in excellent yields (82%-90%). The structures of these trimethylalkylstannanes 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