A new enantioselective route to spiro[piperidine‐3,3′‐oxindoles] from isatin ketimines is described. The aza‐Henry reaction of N‐Boc‐isatin ketimines with methyl 4‐nitrobutyrate in the presence of a Ph2BOX‐CuBr2 complex provided the corresponding nitro amino esters with good diastereoselectivity and excellent enantioselectivity (up to >99% ee). The aza‐Henry adducts were transformed into spiro[piperidine‐3,3′‐oxindoles] after reduction of the nitro group to oxime, and cleavage of the N‐Boc group and lactamisation.