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Nucleophilic epoxidation of gamma-hydroxyvinyl sulfoxide derivatives
Roberto Fernández de la Pradilla1, María Victoria Buergo, Pilar Manzano
1Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain. iqofp19@iqog.csic.es
The Journal of Organic Chemistry
|June 7, 2003
Abstract:
The nucleophilic epoxidation of simple (gamma-silyloxy)vinyl sulfoxides takes place with complete stereocontrol and high yields. For substrates bearing an additional substituent at the gamma position, a reinforcing/nonreinforcing scenario is operative. While E and Z silylated substrates undergo a primarily sulfur directed epoxidation with good to excellent diastereocontrol, the related (E)-(2-methoxyethoxy)methyl ethers display diminished selectivity for the diastereomer derived from the nonreinforcing scenario.