Nucleophilic epoxidation of γ-alkoxy dienyl sulfoxide derivatives |
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Authors: | Roberto Ferná ndez de la Pradilla |
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Affiliation: | Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3; 28006 Madrid, Spain |
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Abstract: | (E,E) and (Z,E) γ-alkoxy dienyl sulfones undergo nucleophilic epoxidation with remarkable regio- and stereoselectivity to render syn oxiranes in a process mainly controlled by the alkoxy stereocenter. Upon epoxidation γ-hydroxy dienyl sulfoxides provide sulfinyl and sulfonyl oxiranes along with bis-epoxides formed through a Payne rearrangement that can be prevented by silylation of the OH group. Interestingly, the presence of a γ-silyloxy group can invert the stereochemical trend of the molecule affording mainly an anti epoxidation process. |
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Keywords: | Sulfoxides Sulfones Dienes Nucleophilic epoxidation |
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