Abstract
We present the synthesis of β-hydroxy sulfonamides derived from d-glucosamine and their application as ligands in titanium tetraisopropoxide promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-trifluoromethylosulfonamido- d-glucosamine derivative is one of the most active ligands known and only 1 mol% of the ligand is sufficient for efficient catalysis of diethylzinc addition. The reaction is highly enantioselective for some aromatic aldehydes and enantiomeric excess up to 99% was obtained.
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