Synthesis of Protected Aminocyclohexanediols

As the model study for the synthesis of aminocyclitols and amino sugars, 2-cyclohexen-1-ol (1) was converted to five of the seven possible (1, 2, 3)-aminocyclohexanediols in protected form (4a, 6a, 11a, 13a, and 18a). Two flexible new approaches were employed: (1) the preparation and iodocyclization of the unsaturated carbonimidothioate 2, and (2) the preparation, rearrangement, and subsequent iodocyclization of unsaturated carbonimidate 8. The alkene functionalization reactions allow a high measure of regio- and stereochemical control over the placement of the eventual amino and hydroxy groups.