title: Chiral phosphoric acid-catalyzed addition of thiols to N-acyl imines: access to chiral N,S-acetals.
abstract: The first catalytic asymmetric method to prepare enantioenriched N,S-acetals using chiral BINOL phosphoric acids is reported. The reaction combines N-acyl imines with thiols to generate products in excellent yield and enantioselectivity. The addition reaction could also be achieved with an exceptional substrate to catalyst (S/C) molar ratio. Electron-rich and electron-deficient aromatic N-acyl imines, as well as a broad range of aliphatic and aromatic thiols, showed excellent reactivity.
authors.affiliation: Department of Chemistry, University of South Florida , 4202 East Fowler Avenue, Tampa, Florida 33620, USA.
authors.forename: Gajendrasingh K
authors.initials: GK
authors.lastname: Ingle
authors.forename: Michael G
authors.initials: MG
authors.lastname: Mormino
authors.forename: Lukasz
authors.initials: L
authors.lastname: Wojtas
authors.forename: Jon C
authors.initials: JC
authors.lastname: Antilla
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000080:Acetals; D007097:Imines; D010756:Phosphoric Acids; D013438:Sulfhydryl Compounds; C030242:phosphoric acid