Sulfinyl-directed diastereoselective |
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Authors: | Lopez Castedo Mascarenas |
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Institution: | Departamento de Quimica Organica, Universidad de Santiago de Compostela, Spain. |
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Abstract: | Introduction of a homochiral p-tolylsulfinyl group at an appropriate position in the alkene accelerates the thermal 5C + 2C] intramolecular cycloaddition to beta-silyloxy-gamma-pyrones and, most importantly, leads to excellent levels of diastereodifferentiation. The resulting adducts can be easily desulfinylated to give optically active 8-oxabicyclic3.2.1]octane intermediates which by virtue of their rich functionalization might be susceptible to elaboration into enantiomerically pure natural products containing seven-membered carbocycles and tetrahydrofurans. |
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