ORGN 107 |
| In the presence of indium metal, 3-iodo-2-[(trimethylsilyl)methyl]propene reacts with sequentially added aldehydes in aqueous media to provide cis-2,6-disubstituted tetrahydropyrans in good yields. It is likely that Lewis-acidic indium salts formed upon allylation of the first equivalent of aldehyde promote a silyl-Prins type reaction with the second equivalent of added aldehyde. The diastereoselective synthesis of cyclopentenyl and cyclohexenyl-fused pyrans via this one-pot, three-component process will also be presented. |
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Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |