title: Organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins.
abstract: The first organocatalytic asymmetric Michael addition of 5H-oxazol-4-ones to nitroolefins has been developed. In the presence of easily prepared L-tert-leucine-derived tertiary amine/thiourea catalyst, the Michael addition of 5H-oxazol-4-ones to nitroolefins proceeded in an excellent diastereo- and enantioselective manner (up to 99% ee and >19:1 dr). The Michael adducts obtained are valuable precursors for the synthesis of chiral α-alkyl-α-hydroxy carboxylic acid derivatives, which represent a series of versatile building blocks in many biologically active compounds.
authors: Institute of Chemical Biology and Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan, P. R. China, 475004, and Waksman Institute of Microbiology, Rutgers, the State University of New Jersey , Piscataway, New Jersey 08854, United States.
authors: Baokun
authors: B
authors: Qiao
authors: Yongqiang
authors: Y
authors: An
authors: Qian
authors: Q
authors: Liu
authors: Wenguo
authors: W
authors: Yang
authors: Hongjun
authors: H
authors: Liu
authors: Juan
authors: J
authors: Shen
authors: Lin
authors: L
authors: Yan
authors: Zhiyong
authors: Z
authors: Jiang
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D002264:Carboxylic Acids; D009574:Nitro Compounds; D010080:Oxazoles