title: Nucleophilic epoxidation of alpha'-hydroxy vinyl sulfoxides.
abstract: The nucleophilic epoxidation of a variety of alpha'-(1-hydroxyalkyl) vinyl sulfones and sulfoxides has been studied. The sulfones give rise to anti oxiranes with modest (E) or excellent (Z) selectivities and in good yields. The (E)-sulfoxides display low reactivity within a reinforcing/nonreinforcing scenario. The use of t-BuOOLi in Et(2)O allows for a highly syn-selective epoxidation-oxidation. The (Z)-sulfoxides display a remarkably high reactivity under these conditions. The reinforcing (S,S(S)) diastereomers (3e-g) yield hydroxy sulfinyl oxiranes with high yields and selectivities. In contrast, the (R,S(S)) diastereomers (4e-g) show diminished reactivities and a very substrate-dependent stereochemical outcome. The structure of these oxiranes has been secured by chemical correlations and an X-ray crystal structure.
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: Jorge
authors.initials: J
authors.lastname: Fernández
authors.forename: Pilar
authors.initials: P
authors.lastname: Manzano
authors.forename: Paloma
authors.initials: P
authors.lastname: Méndez
authors.forename: Julián
authors.initials: J
authors.lastname: Priego
authors.forename: Mariola
authors.initials: M
authors.lastname: Tortosa
authors.forename: Alma
authors.initials: A
authors.lastname: Viso
authors.forename: Martín
authors.initials: M
authors.lastname: Martínez-Ripoll
authors.forename: Ana
authors.initials: A
authors.lastname: Rodríguez