Enantioselective Alkynylation of Aromatic and Aliphatic Aldehydes Catalyzed by Titanium(IV) Complex of D-Glucosamine-derived Sulfonamides
Tomasz Bauer, Maciej Majdecki, Slawomir Smolinskia and Janusz Jurczak
Affiliation: Department of Chemistry, Warsaw University, Pasteura 1, PL-02-093 Warsaw, Poland.
Keywords: Aldehydes, D-glucosamine, dialkylzinc, enantioselective, hexyne-1, phenylacetylene.
We had synthesized a series of β-hydroxy sulfonamides D-glucosamine and applied them as ligands in the titanium
tetraisopropoxide-promoted enantioselective addition of phenylacetylene and hexyne-1 to benzaldehyde and selected aromatic and
aliphatic aldehydes. The N-3,5-bis(ditrifluoromethyl)benzenesulfonamido-D-glucosamine derivative performed best and we choose it as
the most efficient ligand for the addition of phenylacetylene and hexyne-1 to aldehydes. High enantiomeric excesses, up to 96%, were
obtained for some aromatic aldehydes.
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