Regio- and stereocontrol in asymmetric aminohydroxylation reaction on unsaturated azido alcohols

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.1,2 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.3 From this perspective a systematic study about AA reaction, in terms of regio- and chemoselectivity, is being undertaken using Cinchona alkaloids derivatives as chiral ligands (Scheme 1).The substrates chosen for this study are two stereoisomers of the usaturated azido alcohol (1 and 5) identified in our precedent studies as ideal precursor of pyrrolidine ring.4 From this study it was found that the ligands to choose for the achievement of aminoalcoholic products are different depending on the substrate stereochemistry. Once we obtain the aminoalcoholic products is possible to continue the synthesis towards their respective amino iminosugars.