Highly stereoselective epoxidation of alpha-methyl-gamma-hydroxy-alpha,beta-unsaturated esters: rationalization and synthetic applications |
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Authors: | López Irakusne Rodríguez Santiago Izquierdo Javier González Florenci V |
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Affiliation: | Departament de Química Inorgànica i Orgànica Universitat Jaume I, 12080 Castelló, Spain. |
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Abstract: | The diastereoselectivity of the nucleophilic epoxidation of gamma-hydroxy-alpha,beta-unsaturated esters having a methyl substituent at the alpha- or beta-position was investigated. Epoxidation of the alpha-methyl-substituted enoate was highly stereoselective, giving rise to the syn isomer. This finding was used to perform an enantioselective synthesis of a natural product having a beta-hydroxy-alpha-methylene-gamma-butyrolactone motif. The nucleophilic epoxidation of enoates was found to be irreversible. Models to explain the observed stereoselectivities are proposed. |
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