Enantiomeric recognition of α-amino acid derivatives by chiral uranyl–salen receptors. Issue 22 (27th May 2015)

• Record Type: Journal Article
• Authors: Forte, Giuseppe; D'Urso, Alessandro; Ballistreri, Francesco P.; Toscano, Rosa M.; Tomaselli, Gaetano A.; Trusso Sfrazzetto, Giuseppe; Pappalardo, Andrea
• Is Part Of: Tetrahedron letters. Volume 56:Issue 22(2015)
• Page Start: 2922
• Page End: 2926
• Publication Date: 2015-05-27
• Subjects: α-Amino acids -- Enantiomeric recognition -- Host–guest interactions -- Supramolecular complexes -- Uranyl–salen; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.04.092
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: We synthesized two monotopic chiral uranyl–salen receptors1 and2 . We evaluated the enantioselective recognition towards selected α-amino acid salts. Excellent selectivity was obtained between d / l -Trp –TBA pair and the receptor2 . The tert -butyl groups in host2 are involved in the stabilization of the TBA cation. Abstract: Enantioselective molecular recognition of α-amino acid derivatives by two chiral uranyl–salen hosts was investigated by NMR data. The receptors differ for the presence of two tert -butyl groups in the salen backbone. The uranyl hosts have shown high binding constant values and excellent enantioselectivities for the selected guests (up to 100 for the tryptophan derivative).