A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization |
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| Authors: | Daniel P. Canterbury Joann Um Alison J. Frontier |
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| Affiliation: | a Department of Chemistry, University of Rochester, Rochester, NY 14627, United States
b Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569, United States |
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| Abstract: | A mild, convenient reaction sequence for the synthesis of Nazarov cyclization substrates is described. The [3+2] dipolar cycloaddition of a nitrone and an electron-deficient alkyne gives an isolable isoxazoline intermediate, which upon oxidation undergoes stereoselective extrusion of nitrosomethane to give aryl vinyl or divinyl ketones. |
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