title: Organocatalytic enantioselective α-amination of 5-substituted rhodanines: an efficient approach to chiral N,S-acetals.
abstract: We report a highly efficient approach to constructing chiral N,S-acetals using 5-substituted rhodanines as sulfur-bound pronucleophiles catalyzed by natural cinchona alkaloids quinine or quinidine. This α-amination reaction has a broad substrate scope, and the products featuring both rhodanine and N,S-acetal structural motifs were obtained in high yields and excellent enantioselectivities.
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, P. R. China. bmwang@dlut.edu.cn.
authors.forename: Huanrui
authors.initials: H
authors.lastname: Zhang
authors.forename: Baomin
authors.initials: B
authors.lastname: Wang
authors.forename: Longchen
authors.initials: L
authors.lastname: Cui
authors.forename: Ying
authors.initials: Y
authors.lastname: Li
authors.forename: Jingping
authors.initials: J
authors.lastname: Qu
authors.forename: Yuming
authors.initials: Y
authors.lastname: Song
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D009930:Organic Chemicals; D010406:Penicillins / Q000138:chemical synthesis / Q000737:chemistry; D012236:Rhodanine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D002930:Cinchona Alkaloids; D009930:Organic Chemicals; D010406:Penicillins; D012236:Rhodanine