Highly diastereoselective synthesis of (E)-1-iodo-1-trimethylgermyl-1-alkenes via the hydroalumination of 1-trimethylgermyl-1-alkynes followed by reaction with N-iodosuccinimide

ORGN 397

Narayan G. Bhat, nbhat@panam.edu1, Jessica I. Lopez1, and Atenea A. Garza2. (1) Department of Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541, (2) Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541
A highly diastereoselective synthesis of (E)-1-iodo-1-trimethylgermyl-1-alkenes via the hydroalumination of the corresponding 1-trimethylgermyl-1-alkynes with diisobutylaluminum hydride (DIBAL-H) in hexanes followed by iodination with N-iodosuccinimide in tetrahydrofuran is presented. 1-Trimethylgermyl-1-alkynes (easily prepared by the deprotonation of the corresponding terminal alkynes with n-butyllithium followed by germylation with trimethylgermanium bromide) smoothly undergo hydroalumination with DIBAL-H in hexanes at room temperature for 16 h. The iodination of the resulting intermediates with N-iodosuccinimide in tetrahydrofuran at 0oC provides the corresponding (E)-1-iodo-1-trimethylgermyl-1-alkenes in good yields (76%-84%) and in high stereochemical purities (> 98%) as evidenced 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