Treatment of 4-amino-4-phenyl-butan-2-ol with mesyl chloride,
followed by displacement with amine nucleophiles resulted in a 1,3
rearrangement via an azetidinium cation intermediate. This rearrangement
has been proven to proceed via a double inversion of stereocentres
at positions 1 and 3.
amines - azetidinium cation - double inversion - nucleophiles - rearrangement
