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Enantioselective Alkynylation of Aromatic and Aliphatic Aldehydes Catalyzed by Titanium(IV) Complex of D-Glucosamine-derived Sulfonamides

Author(s): 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.

Graphical Abstract:


Abstract:

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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Article Details

VOLUME: 18
ISSUE: 9
Page: [1218 - 1224]
Pages: 7
DOI: 10.2174/1385272819999140521123706