Enantioselective addition of phenylacetylene to aldehydes catalyzed by a d-glucosamine-derived sulfonamide–titanium complex

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)benzenesulfo...

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Veröffentlicht in:	Tetrahedron letters 2011-09, Vol.52 (38), p.4882-4884
Hauptverfasser:	Bauer, Tomasz, Smoliński, Sławomir, Gaweł, Przemysław, Jurczak, Janusz
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes Aliphatic compounds Benzaldehyde Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Catalysis Catalysts: preparations and properties Chemistry d-Glucosamine Derivatives Enantioselective Exact sciences and technology General and physical chemistry Ligands Organic chemistry Phenylacetylene Preparations and properties Synthesis (chemistry) Tetrahedrons Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry Titanium
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Zusammenfassung:	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.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2011.07.051