ORGN 130 |
| Narayan G. Bhat and Edmundo Lozano. Chemistry, University of Texas-Pan American, 1201 West University Drive, Edinburg, TX 78541 |
| A highly diastereoselective synthesis of (Z)-chloro-1-trimethylgermyl-1-alkenes via the hydrozirconation of the corresponding 1-trimethylgermyl-1-alkynes with bis(cyclopentadienyl)zirconium chloride hydride (Schwartz's reagent) followed by chlorination with N-chlorosuccinimide is presented. 1-Trimethylgermyl-1-alkynes (easily prepared by the deprotonation of the corresponding alkynes followed by germylation with trimethylgermyl bromide) smoothly undergo hydrozirconation with Schwartz's reagent in dichloromethane. The chlorination of the resulting intermediates with N-chlorosuccinimide (NCS) in tetrahydrofuran at 0oC provides the corresponding (Z)-1-chloro-1-trimethylgermyl-1-alkenes in good yields (78%-84%) and in high stereochemical purities (> 98%) as evidenced by NMR spectral data. |
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |