Nucleophilic epoxidation of alpha'-hydroxy dienyl sulfoxides |
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Authors: | Fernández de la Pradilla Roberto Manzano Pilar Montero Carlos Priego Julián Martínez-Ripoll Martín Martínez-Cruz Luis A |
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Institution: | Instituto de Química Orgánica, CSIC, Juan de la Cierva, 3, 28006 Madrid, Spain. iqofp19@iqog.csic.es |
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Abstract: | A novel route to enantiopure densely functionalized epoxy sulfinyl tetrahydrofurans, based on the unexpected and highly stereoselective remote nucleophilic epoxidation of hydroxy 1-sulfinyl butadienes with t-BuOOK, followed by ring closure and subsequent epoxidation of the resulting sulfinyl dihydrofurans, is described. Alternatively, the treatment of these dienes with m-CPBA followed by acid-catalyzed cyclization gives rise to related sulfonyl dihydrofurans in high yields but with low selectivity. The stereochemical outcome of the nucleophilic epoxidation of these substrates has also been studied. |
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