Azetidine Iminosugars from the Cyclization of 3,5-Di-<i>O</i>-triflates of α-Furanosides and of 2,4-Di-<i>O</i>-triflates of β-Pyranosides Derived from Glucose

Primary amines with either 3,5-di-<i>O</i>-ditriflates of α-furanosides or 2,4-di-<i>O</i>-triflates of β-pyranosides form bicyclic azetidines in high yield

Synthesis from d‑Altrose of (5<i>R</i>,6<i>R</i>,7<i>R</i>,8<i>S</i>)‑5,7-Dihydroxy-8-hydroxymethylconidine and 2,4-Dideoxy-2,4-imino‑d‑glucitol, Azetidine Analogues of Swainsonine and 1,4-Dideoxy-1,4-imino‑d‑mannitol

Ring closure of a 3,5-di-<i>O</i>-triflate derived from d-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine