(DHQD)2PHAL-catalyzed diastereoselective and enantioselective chlorocyclization reactions of bisallylic amides were achieved with N-chlorophthalimide (NCP) as the chlorinating reagent. A series of chlorinated oxazines bearing three contiguous chiral centers were obtained in high yields (up to 99%), high diastereoselectivity and excellent enantioselectivity (up to 99% ee).