title: Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols.
abstract: A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The resulting β-hydroxyl sulfides are obtained in excellent yield and enantioselectivity.
authors.affiliation: Department of Chemistry, University of South Florida , 4202 East Fowler Avenue, Tampa, Florida 33620, United States.
authors.forename: Gajendrasingh
authors.initials: G
authors.lastname: Ingle
authors.forename: Michael G
authors.initials: MG
authors.lastname: Mormino
authors.forename: Jon C
authors.initials: JC
authors.lastname: Antilla
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C406944:BINOL, naphthol; D004852:Epoxy Compounds; D009284:Naphthols; D013438:Sulfhydryl Compounds; D008094:Lithium