Asymmetric synthesis of beta-hydroxy sulfides controlled by remote sulfoxides.
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).
Arroyo
Yolanda
Y
Departamento de Química OrgAnica (ETSII), Universidad de Valladolid, Paseo del Cauce s/n, 47011 Valladolid, Spain.
Rodríguez
J Félix
JF
Santos
Mercedes
M
Tejedor
M Ascensión Sanz
MA
Ruano
José Luis García
JL
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*
D001555:Benzene Derivatives; D002254:Carbonates; D013438:Sulfhydryl Compounds; D013440:Sulfides; D013452:Sulfonium Compounds; D013454:Sulfoxides