title: Catalytic asymmetric synthesis of thiols.
abstract: The synthesis of enantiopure thiols is of significant interest for industrial and academic applications. However, direct asymmetric approaches to free thiols have previously been unknown. Here we describe a novel organocascade that is catalyzed by a confined chiral phosphoric acid and furnishes O-protected β-hydroxythiols with excellent enantioselectivities. The method relies on an asymmetric thiocarboxylysis of meso-epoxides, followed by an intramolecular trans-esterification reaction. By varying the reaction conditions, the intermediate thioesters can also be obtained chemoselectively and enantioselectively.
authors.affiliation: Max-Planck-Institut für Kohlenforschung , Kaiser-Wilhelm Platz 1, 45470 Mülheim an der Ruhr, Germany.
authors.forename: Mattia Riccardo
authors.initials: MR
authors.lastname: Monaco
authors.forename: Sébastien
authors.initials: S
authors.lastname: Prévost
authors.forename: Benjamin
authors.initials: B
authors.lastname: List
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010756:Phosphoric Acids; D013438:Sulfhydryl Compounds; C030242:phosphoric acid