ORGN 621 |
β-Acyloxysulfonyl tethers for intramolecular Diels-Alder cycloaddition reactions
| Nataliya Chumachenko and Paul Sampson. Department of Chemistry, Kent State University, Kent, OH 44242 |
| We have found a convenient synthetic entry to previously unknown sulfone-based tethers for intramolecular Diels-Alder cycloaddition reactions. Readily available Zn (E)-sulfinate 1 reacts with propylene oxide regioselectively to form β-(dienylsulfonyl) alcohol 2. Acylation with various α-substituted acrylic acids followed by thermally mediated Diels-Alder cycloaddition in toluene at 120 oC affords only endo-cycloadducts 3 in good yield with complete regioselectivity. In each case, the major diastereomer can be easily separated from the crude reaction mixture by crystallization or column chromatography. Current efforts are directed toward establishing the scope and limitations of this chemistry and exploring the potential synthetic utility of the resulting cycloadducts 3. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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