title: Asymmetric synthesis of benzylic quaternary difunctionalized carbons mediated by a remote sulfinyl group.
abstract: Enantiomerically enriched α-aryl α-cyanoacetates and α-aryl α-acylacetonitriles bearing a benzylic quaternary stereocenter have been readily synthesized by stereoselective reaction of 2-alkyl-2-[2-(p-tolylsulfinyl)phenyl]acetonitriles with different acylating and alkoxycarbonylating reagents under basic conditions. The stereoselectivity of the reactions proved closely dependent on the nature of the intermediate carbanionic species, the evolution of which was effectively controlled by a sulfinyl group as a remote chiral auxiliary.
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es
authors.forename: José Luis García
authors.initials: JL
authors.lastname: Ruano
authors.forename: Esther
authors.initials: E
authors.lastname: Torrente
authors.forename: Ana M
authors.initials: AM
authors.lastname: Martín-Castro
mesh_terms: D001554:Benzene / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D013454:Sulfoxides; D002244:Carbon; D001554:Benzene