ORGN 95 |
| 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 dichloromethane followed by iodination with iodine is presented. 1-Trimethylgermyl-1-alkynes (easily prepared by the deprotonation of the corresponding alkynes followed by germylation with trimethylgermyl bromide) smoothly undergo hydroalumination with DIBAL-H in dichloromethane at room temperature for 16 h.. The iodination of the resulting intermediates with iodine in tetrahydrofuran at 0 oC provides the corresponding (E)-1-iodo-1-trimethylgermyl-1-alkenes in good yields (72%-84%) and in high stereochemical purities (> 98%). |
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Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster
Division of Organic Chemistry |