Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization.

Article abstract of DOI:10.1016/S0040-4039(00)77602-7

N-tosyl-oxiraneethylamines undergo cyclization upon treatment with aqueous sodium hydroxide to afford either N-tosyl-azetidinemethanols or N-tosyl-pyrrolidin-3-ols in high yields. The change in regioselectivity of this cyclization process is quite dependent on the location of a pentamethylene substitution in the chain connecting the nitrogen with the oxirane ring.