Chiral benzoxazinones and 4-3,1-benzoxazines as important motifs are widely found in abundant pharmaceuticals and biological molecules. We herein successfully developed the first kinetic resolution (KR) process of racemic benzoxazinones through Ir-catalyzed asymmetric intramolecular allylation, furnishing a wide range of chiral benzoxazinones and 4-3,1-benzoxazines with excellent results via outstanding KR performances (with the factor up to 170). This protocol exhibited broad substrate scope generality and good functional group tolerance, and the chiral 4-3,1-benzoxazine products could be readily transformed to other useful optically active heterocycles.
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