t-BuOK mediated the dehydrohalogenation of chloromethylmorpholine regioisomers 30 and 34 to provide exocyclic enol ethers 32 and 43, respectively, in good yields (Scheme 8). Iodoacetalization proceeded efficiently on both enol ethers. No stereoinduction was observed in the reaction of 5-methyl-substituted enol ether 43; the iodoacetal product 44 was isolated as a 1:1 mixture of diastereoisomers. Moving the methyl substituent to the 6-position of the morpholine ring (32) led to modest diastereoselectivity, with iodoacetal 45 now formed as a 4:1 mixture of diastereoisomers. In both cases, the diastereoisomeric ratio did not change when the reaction was performed at lower temperature (0 °C or -78 °C).