Evaluation of chiral recognition ability of a novel uranyl-salophen-based receptor: An easy and rapid testing protocol

Chemistry - A European Journal

Volumn 10, Issue 13, 2004, Pages 3301-3307

  Dalla Cort, Antonella ^a   Miranda Murua, José Ignacio ^b   Pasquini, Chiara ^a   Pons, Miquel ^b   Schiaffino, Luca ^a,b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Chirality enantioselective recognition; High throughput screening; Host guest systems; NMR spectroscopy

Indexed keywords

AMINES; CHEMICAL ANALYSIS; COMBINATORIAL MATHEMATICS; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY; RACEMIZATION;

AMMONIUM COMPOUNDS;

ACETAMINOSALOL; AMINE; AMMONIUM CHLORIDE; QUATERNARY AMMONIUM DERIVATIVE; RECEPTOR; SULFOXIDE; URANIUM DERIVATIVE;

ARTICLE; CHIRALITY; COMBINATORIAL CHEMISTRY; ENANTIOMER; ENANTIOSELECTIVITY; EVALUATION; ISOMERISM; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; SCREENING; SYNTHESIS;

BENZOPHENONES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; PHENETHYLAMINES; SALICYLIC ACIDS; STEREOISOMERISM; SULFOXIDES;

EID: 3142747694     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400016     Document Type: Article

References (44)

1. a) T. H. Webb, C. S. Wilcox, Chem. Soc. Rev. 1993, 22, 383-395;
2. b) J.-M. Lehn Supramolecular Chemistry, VCH, Weinheim, 1995;
3. c) X. X. Zhang, J. S. Bradshaw, R. M. Izatt, Chem. Rev. 1997, 97, 3313-3362;
4. d) H. Ogoshi, T. Mizutani, Acc. Chem. Res. 1998, 31, 81-89.
5. a) V. Boehmer, D. Kraft, M. Tabatabai, J. Inclusion Phenom. 1994, 17-39, and references therein.
6. b) C. D. Gutsche, Calixarenes Revisited, The Royal Society of Chemistry, Cambridge, 1998, pp. 136-142.
7. a) E. E. Simanek, S. Qiao, I. S. Choi, G. M. Whitesides, J. Org. Chem. 1997, 62, 2619-2621;
8. b) J. M. Rivera, T. Martin, J. Rebek, Jr., Science 1998, 279, 1021-1023;
9. c) R. K. Castellano, C. Nuckolls, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 11156-11163;
10. d) T. Ishi-i, M. Crego-Calama, P. Timmerman, D. N. Reinhoudt, S. Shinkai, Angew. Chem. 2002, 114, 2004-2009; Angew. Chem. Int. Ed. 2002, 41, 1924-1929;
11. d) T. Ishi-i, M. Crego-Calama, P. Timmerman, D. N. Reinhoudt, S. Shinkai, Angew. Chem. 2002, 114, 2004-2009; Angew. Chem. Int. Ed. 2002, 41, 1924-1929;
12. e) L. J. Prins, F. De Jong, P. Timmerman, D. N. Reinhoudt, Nature 2000, 408, 181-184;
13. f) J. M. C. A. Kerckhoffs, F. W. B. van Leeuwen, A. L. Spek, H. Kooijman, M. Crego-Calama, D. N. Reinhoudt, Angew. Chem. 2003, 115, 5895-5900; Angew. Chem. Int. Ed. 2003, 42, 5717-5722.
14. f) J. M. C. A. Kerckhoffs, F. W. B. van Leeuwen, A. L. Spek, H. Kooijman, M. Crego-Calama, D. N. Reinhoudt, Angew. Chem. 2003, 115, 5895-5900; Angew. Chem. Int. Ed. 2003, 42, 5717-5722.
15. a) D. Parker, Chem. Rev. 1991, 91, 1441-1457;
16. b) M. T. Reetz, Angew. Chem. 2001, 113, 292-320; Angew. Chem. Int. Ed. 2001, 40, 284-310;
17. b) M. T. Reetz, Angew. Chem. 2001, 113, 292-320; Angew. Chem. Int. Ed. 2001, 40, 284-310;
18. c) M. T Reetz, Angew. Chem. 2002, 114, 1391-1394; Angew. Chem. Int. Ed. 2002, 41, 1335-1338;
19. d) M. Tsukamoyo, H. B. Kagan, Adv. Synth. Catal. 2002, 344, 453-463;
20. e) P. Tielmann, M. Boese, M. Luft, M. T. Reetz, Chem. Eur. J. 2003, 9, 3882-3887;
21. f) R. E. Heath, G. M. Dykes, H. Fish, D. K. Smith, Chem. Eur. J. 2003, 9, 850-855.
22. V. van Axel Castelli, A. Dalla Cort, L. Mandolini, V. Pinto, D. N. Reinhoudt, F. Ribaudo, C. Sanna, L. Schiaffino, B. H. M. Snellink-Ruël, Supramol. Chem. 2002, 14, 211-219.
23. a) P. Pfeiffer, T. Hesse, H. Pfitzner, W. Scholl, H. Thielert, J. Prakt. Chem. 1937, 149, 217-295;
24. b) G. Bandoli, D. A. Clemente, U. Croatto, M. Vidali, P. A. Vigato, J. Chem. Soc. Chem. Commun. 1971, 1330-1331.
25. "Metallomacrocycles and -Clefts: Receptors for Neutral Molecules and Anions": D. M. Rudkevich, W. T. S. Huck, F. C. J. M. van Veggel, D. N. Reinhoudt, NATO ASI Ser. Ser. C 1994, 448, 329-349.
26. "Molecular Recognition of Neutral Molecules by Synthetic Receptors": A. R. Van Doorn, W. Verboom, D. N. Reinhoudt Adv. Supramol. Chem. 1993, 3, 159-206.
27. a) C. J. van Staveren, E. F. Fenton, D. N. Reinhoudt, J. van Eerden, S. Harkema, J. Am. Chem. Soc. 1987, 109, 3456-3458;
28. b) M. Cametti, M. Nissinen, A. Dalla Cort, L. Mandolini, K. Rissanen, Chem. Commun. 2003, 2420-2421.
29. a) V. van Axel Castelli, R. Cacciapaglia, G. Chiosis, F. C. J. M. van Veggel, L. Mandolini, D. N. Reinhoudt, Inorg. Chim. Acta 1996, 246, 181-193;
30. b) V. van Axel Castelli, A. Dalla Cort, L. Mandolini, D. N. Reinhoudt, J. Am. Chem. Soc. 1998, 120, 12688-12689;
31. c) V. van Axel Castelli, A. Dalla Cort, L. Mandolini, D. N. Reinhoudt, L. Schiaffino, Chem. Eur. J. 2000, 6, 1193-1198;
32. d) V. van Axel Castelli, A. Dalla Cort, L. Mandolini, D. N. Reinhoudt, L. Schiaffino, Eur. J. Org. Chem. 2003, 627-633.
33. L. A. J. Chrisstoffels, F. de Jong, D. N. Reinhoudt, Chem. Eur. J. 2000, 6, 1376-1385.
34. M. M. G. Antonisse, B. H. M. Snellink-Ruël, J. F. J. Engbersen, D. N. Reinhoudt, J. Org. Chem. 1998, 63, 9776-9781.
35. a) C. J. van Staveren, J. van Eerden, F. C. J. M. van Veggel, S. Harkema, D. N. Reinhoudt, J. Am. Chem. Soc. 1988, 110, 4994-5008;
36. b) D. N. Reinhoudt, H. J. den Hertog, Jr., Bull. Soc. Chim. Belg. 1988, 97, 645-653;
37. c) A. R. van Doorn, R. Schaafstra, M. Bos, S. Harkema, J. van Eerden, W. Verboom, D. N. Reinhoudt, J. Org. Chem. 1991, 56, 6083-6094;
38. d) A. R. van Doorn, W. Verboom, S. Harkema, D. N. Reinhoudt, Synthesis 1992, 119-122;
39. e) D. M. Rudkevich, W. P. R. V. Stauthamer, W. Verboom, J. F. J. Engbersen, S. Harkema, D. N. Reinhoudt, J. Am. Chem. Soc. 1992, 114, 9671-9673.
40. A. Dalla Cort, L. Mandolini, G. Palmieri, C. Pasquini, L. Schiaffino, Chem. Commun. 2003, 2178-2179.
41. Between the two chiral primary amines, we chose to carry out titrations only with guest 5 as it shows the highest selectivity.
42. H. Hart, J. W. Link, J. Org. Chem. 1969, 34, 758-760.
43. E. Verner, B. A. Katz, J. R. Spencer, D. Allen, J. Hataye, W. Hruzewicz, H. C. Hui, A. Kolesnikov, Y. Li, C. Luong, A. Martelli, K. Radika, R. Rai, M. She, W. Shrader, P. A. Sprengeler, S. Trapp, J. Wang, W. B. Young, R. L. Mackman, J. Med. Chem. 2001, 44, 2753-2771.
44. F. M. Dean, A. G. Herbin, D. A. Matkin, A. W. Price, M. L. Robinson, J. Chem. Soc. Perkin Trans. 1 1980, 1986-1993.