Study of asymmetric aminohydroxylation reaction aimed at the synthesis of aminoiminosugars

Recently, the amino derivatives of the iminosugars have stimulated significant interest for their higher efficiency and selectivity in the inibition of some enzymes compared to their analogous iminosugars . In this work we propose a synthetic strategy for the stereocontrolled preparation of pyrrolidine amino iminosugars, using asymmetric aminohydroxylation reaction (AA) as the key step. From this perspective a systematic study about AA reaction, in terms of regio- and chemoselectivity, is being undertaken using Cinchona derivatives alkaloids as chiral ligands. The substrate chosen for this study is the usaturated azido alchol 1, identified in our precedent studies as the ideal precursor of pyrrolidinic ring. From this study it was found that the best ligand is (DHQ)2PHAL which is the one to chose for the synthesis of the amino iminosugar.