title: Organocatalytic oxyamination of azlactones: kinetic resolution of oxaziridines and asymmetric synthesis of oxazolin-4-ones.
abstract: The first example of oxyamination of azlactones with oxaziridines was realized using a chiral bisguanidinium salt. Efficient catalytic asymmetric oxyamination and kinetic resolution of oxaziridines occurred simultaneously. Various chiral oxazolin-4-one derivatives with potential biological activity were obtained (up to 92% ee). Meanwhile, a series of optically pure oxaziridines were recovered with up to 99% ee and successfully used in the asymmetric oxyamination of 3-methyl-1H-indole and styrene. The triple stereodifferentiation process was also studied via control experiments.
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
authors.forename: Shunxi
authors.initials: S
authors.lastname: Dong
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Yin
authors.initials: Y
authors.lastname: Zhu
authors.forename: Peng
authors.initials: P
authors.lastname: He
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000586:Amination; D001388:Aziridines / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010081:Oxazolone / Q000737:chemistry*
chemical_list: D001388:Aziridines; D001391:Azo Compounds; D007783:Lactones; D010081:Oxazolone