title: Catalytic asymmetric conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones with bifunctional catalysts.
abstract: In this communication, we describe an unprecedented highly enantioselective catalytic conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones catalyzed by acid-base bifunctional catalysis. This reaction provides a useful catalytic method for the synthesis of optically active chiral sulfur compounds that are otherwise difficult to prepare by asymmetric catalysis. The successful development of this reaction resulted from a discovery that, upon proper modification, a cinchona alkaloid bearing a thiourea functionality at 6' position can afford highly efficient catalysis for asymmetric conjugate additions.
authors.affiliation: Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
authors.forename: Yan
authors.initials: Y
authors.lastname: Liu
authors.forename: Bingfeng
authors.initials: B
authors.lastname: Sun
authors.forename: Baomin
authors.initials: B
authors.lastname: Wang
authors.forename: Matthew
authors.initials: M
authors.lastname: Wakem
authors.forename: Li
authors.initials: L
authors.lastname: Deng
mesh_terms: D000215:Acylation; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002930:Cinchona Alkaloids; D004952:Esters; D023303:Oxazolidinones; D013438:Sulfhydryl Compounds