Enantioselective addition of phenylacetylene to aldehydes catalyzed by a d-glucosamine-derived sulfonamide-titanium complex |
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| Authors: | Tomasz Bauer S?awomir SmolińskiPrzemys?aw Gawe? Janusz Jurczak |
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| Institution: | a Department of Chemistry, Warsaw University, Pasteura 1, PL-02-093 Warsaw, Poland
b Institute of Organic Chemistry, Polish Academy of Science, Kasprzaka 44/52, 01-224 Warsaw, Poland |
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| 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 phenylacetylene to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-3,5-bis(trifluoromethyl)benzenesulfonamido-d-glucosamine derivative was chosen as the most efficient ligand for this addition. The reaction is highly enantioselective for several aromatic aldehydes and enantiomeric excesses up to 92% were obtained. |
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| Keywords: | d-Glucosamine" target="_blank">d-Glucosamine Aldehydes Phenylacetylene Enantioselective |
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