Chiral benzoxazinones and 4H-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 4H-3,1-benzoxazines with excellent
results via outstanding KR performances (with the s factor up to 170). This protocol exhibited broad substrate scope
generality and good functional group tolerance, and the chiral 4H-3,1-benzoxazine products could be readily transformed
to other useful optically active heterocycles.
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