Nucleophilic ring closure and opening of aminoiodohydrins

Enantiopure aminoiodohydrins obtained from α-aminoaldehydes and Sm/CH2I2 have been transformed into regioisomeric aminoiodohydrins, aminoepoxides, azetidines or 1,3-oxazolidines. The key step in these transformations is a nucleophilic opening–closing process.