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An unusual decarboxylative photocyclization of 2-acyl benzamides with intramolecular chiral α-aminoacids was studied. The reaction exclusively yields bi- and tri-cyclic benzo-oxazepines via distinct chemoselective C–O bond formation. High enantio- and diastereo-selectivities (ee=87–99% and dr=85/15–95/5) for the products were achieved. Evidence indicates that the formation of the two chiral carbon centers is controlled by chiral memory.