title: Nucleophilic epoxidation of gamma-hydroxyvinyl sulfoxide derivatives.
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.
authors.affiliation: Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain. iqofp19@iqog.csic.es
authors.forename: Roberto
authors.initials: R
authors.lastname: Fernández de la Pradilla
authors.forename: María Victoria
authors.initials: MV
authors.lastname: Buergo
authors.forename: Pilar
authors.initials: P
authors.lastname: Manzano
authors.forename: Carlos
authors.initials: C
authors.lastname: Montero
authors.forename: Julián
authors.initials: J
authors.lastname: Priego
authors.forename: Alma
authors.initials: A
authors.lastname: Viso
authors.forename: Félix H
authors.initials: FH
authors.lastname: Cano
authors.forename: María Paz
authors.initials: MP
authors.lastname: Martínez-Alcázar