Synthesis of a chiral 2,6-bridged morpholine system: trans-6,7-Diol derivatives of 8-oxa-3-azabicyclo[3.2.1]octane

Article abstract of DOI:10.1016/0040-4020(94)00957-V

The title compound 6, [1R-(6endo,7exo)]-8-oxa-3-azabicyclo[3.2.1]octane-6,7-diol, was derived in nine steps from 1-amino-1-deoxy-D-glucitol 2. The key step was the acid catalyzed rearrangement of epoxide 3 to the 2,5-cis-disposed hydrofuran compound 5. Li