title: Asymmetric synthesis of beta-hydroxy sulfides controlled by remote sulfoxides.
abstract: Reactions of (S)-alpha-(methylthio)-2-(p-tolylsulfinyl)benzyl carbanion with different carbonyl compounds proceeds with complete control of the configuration at the benzylic position. Aldehydes yield easily separable mixtures of beta-hydroxy sulfides, epimers at the hydroxylic carbon, where the stereoselectivity depends on steric factors (from 20% to >98% de).
authors.affiliation: Departamento de Química OrgAnica (ETSII), Universidad de Valladolid, Paseo del Cauce s/n, 47011 Valladolid, Spain.
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Arroyo
authors.forename: J Félix
authors.initials: JF
authors.lastname: Rodríguez
authors.forename: Mercedes
authors.initials: M
authors.lastname: Santos
authors.forename: M Ascensión Sanz
authors.initials: MA
authors.lastname: Tejedor
authors.forename: José Luis García
authors.initials: JL
authors.lastname: Ruano
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D008956:Models, Chemical; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013440:Sulfides / Q000138:chemical synthesis*; D013452:Sulfonium Compounds / Q000737:chemistry; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D002254:Carbonates; D013438:Sulfhydryl Compounds; D013440:Sulfides; D013452:Sulfonium Compounds; D013454:Sulfoxides