Stereoselective synthesis of 3-hydroxyazetidines via regioselective halogenation of 2,3-epoxyamines by using magnesium bromide

Article abstract of DOI:10.1016/S0040-4039(97)01360-9

A novel stereoselective synthesis of 3-hydroxyazetidines starting from 2,3-epoxyamines is described. Regioselectivity of the intramolecular cyclization of 2,3-epoxyamines is controlled by the use magnesium bromide. The cyclization proceeds with retention of the stereochemistry, caused by double inversion of two sequential S(N)2 reactions of the epoxyamines.