Organocatalytic Oxyamination of Azlactones: Kinetic Resolution of Oxaziridines and Asymmetric Synthesis of Oxazolin-4-ones

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.