Novel IBX-Mediated Processes for the Synthesis of Amino Sugars and Libraries Thereof

The cyclization of N-arylcarbamates onto olefins, orchestrated by IBX, is a new synthetic method for the preparation of diverse arrays of amino sugar building blocks (see scheme for an example). A revised proposal for the mechanism of this novel reaction is also disclosed, which leads to the discovery of a remarkable interaction of IBX and glycals. The new reactions have potential in the production of libraries for biological screening. IBX=o-iodoxybenzoic acid = 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide.