New ligands for enantioselective recognition of chiral carboxylates based on 1,1′-binaphthalene-2,2′-diamine

Collection of Czechoslovak Chemical Communications

Volumn 69, Issue 2, 2004, Pages 365-383

  Stibor, Ivan ^a   Holakovský, Roman ^a   Mustafina, Asiya R ^b   Lhoták, Pavel ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

^b A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

Amides; Axial chirality; Biaryls; Binaphthalenes; Chiral anion recognition; Complexation; Extractions

Indexed keywords

1,1' BINAPHTHALENE 2,2' DIAMINE; 1,1' BINAPHTHYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIAMINE DERIVATIVE; LIGAND; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 1642501735     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20040365     Document Type: Article

References (50)

1. a) Gale P. A.: Coord. Chem. Rev. 2003, 240, 191;
2. b) Gale P. A.: Coord. Chem. Rev. 2001, 213, 79;
3. c) Gale P. A.: Coord. Chem. Rev. 2000, 199, 181;
4. d) Beer P. D., Hayes E. J.: Coord. Chem. Rev. 2003, 240, 167;
5. e) Best M. D., Tobey S. L., Anslyn E. V.: Coord. Chem. Rev. 2003, 240, 3;
6. f) Gale P. A., Beer P. D.: Angew. Chem., Int. Ed. 2001, 40, 487;
7. g) Bianchi A., Bowman-James K., Garcia-Espana E. (Eds): Supramolecular Chemistry of Anions. Wiley-VCH, New York 1997;
8. h) Hartley J. H., James T. D., Ward C. J.: J. Chem. Soc., Perkin Trans. 1 2000, 3155;
9. i) Schmidtchen F. P., Berger M.: Chem. Rev. 1997, 97, 1609.
10. Smith D. K.: Org. Biomol. Chem. 2003, 1, 3874.
11. a) Bondy C. R., Loeb S. J.: Coord. Chem. Rev. 2003, 240, 77;
12. b) Choi K., Hamilton A. D.: Coord. Chem. Rev. 2003, 240, 101;
13. c) Antonisse M. M. G., Reinhoudt D. N.: Chem. Commun. 1998, 443;
14. d) Herges R., Dikmans A., Jana U., Koehler F., Jones P. G., Dix I., Fricke T., Koenig B.: Eur. J. Org. Chem. 2002, 3004;
15. e) Shogemori K., Nishizawa S., Yokobori T., Shioya T., Teramae N.: New J. Chem. 2002, 26, 1102;
16. f) Werner F., Schneider H. J.: Helv. Chim. Acta 2000, 83, 465.
17. a) Budka J., Lhoták P., Michlová V., Stibor I.: Tetrahedron Lett. 2001, 42, 1583;
18. b) Št́astný V., Lhoták P., Michlová V., Stibor I., Sykora J.: Tetrahedron 2002, 58, 7207;
19. Dudič M., Lhoták P., Stibor I., Lang K., Prošková P.: Org. Lett. 2003, 5, 149.
20. Stibor I., Dana S. M. H., Lhoták P., Hodačová J., Koča J., Čajan M.: Gazz. Chim. Ital. 1997, 127, 673.
21. a) Čajan M., Stibor I., Koča J.: J. Phys. Chem. A 1999, 103, 3778;
22. b) Čajan M., Damborský J., Stibor I., Koča J.: J. Chem. Inf. Comput. Sci. 2000, 40, 1151.
23. For books on calixarenes see: a) Asfari Z., Böhmer V., Harrowfield J., Vicens J. (Eds): Calixarenes 2001. Kluwer Academic Publishers, Dordrecht 2001; b) Mandolini L., Ungaro R.: Calixarenes in Action. Imperial College Press, London 2000; c) Gutsche C. D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge 1998; d) Vicens J., Asfari Z., Harrowfield J. M. (Eds): Calixarenes 50th Aniversary: Commemorative Issue. Kluwer Academic Publishers, Dordrecht 1994; e) Vicens J., Böhmer V. (Eds): Calixarenes: A Versatile Class of Macrocyclic Compounds. Kluwer Academic Publishers, Dordrecht 1991.
24. For books on calixarenes see: a) Asfari Z., Böhmer V., Harrowfield J., Vicens J. (Eds): Calixarenes 2001. Kluwer Academic Publishers, Dordrecht 2001; b) Mandolini L., Ungaro R.: Calixarenes in Action. Imperial College Press, London 2000; c) Gutsche C. D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge 1998; d) Vicens J., Asfari Z., Harrowfield J. M. (Eds): Calixarenes 50th Aniversary: Commemorative Issue. Kluwer Academic Publishers, Dordrecht 1994; e) Vicens J., Böhmer V. (Eds): Calixarenes: A Versatile Class of Macrocyclic Compounds. Kluwer Academic Publishers, Dordrecht 1991.
25. For books on calixarenes see: a) Asfari Z., Böhmer V., Harrowfield J., Vicens J. (Eds): Calixarenes 2001. Kluwer Academic Publishers, Dordrecht 2001; b) Mandolini L., Ungaro R.: Calixarenes in Action. Imperial College Press, London 2000; c) Gutsche C. D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge 1998; d) Vicens J., Asfari Z., Harrowfield J. M. (Eds): Calixarenes 50th Aniversary: Commemorative Issue. Kluwer Academic Publishers, Dordrecht 1994; e) Vicens J., Böhmer V. (Eds): Calixarenes: A Versatile Class of Macrocyclic Compounds. Kluwer Academic Publishers, Dordrecht 1991.
26. For books on calixarenes see: a) Asfari Z., Böhmer V., Harrowfield J., Vicens J. (Eds): Calixarenes 2001. Kluwer Academic Publishers, Dordrecht 2001; b) Mandolini L., Ungaro R.: Calixarenes in Action. Imperial College Press, London 2000; c) Gutsche C. D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge 1998; d) Vicens J., Asfari Z., Harrowfield J. M. (Eds): Calixarenes 50th Aniversary: Commemorative Issue. Kluwer Academic Publishers, Dordrecht 1994; e) Vicens J., Böhmer V. (Eds): Calixarenes: A Versatile Class of Macrocyclic Compounds. Kluwer Academic Publishers, Dordrecht 1991.
27. For books on calixarenes see: a) Asfari Z., Böhmer V., Harrowfield J., Vicens J. (Eds): Calixarenes 2001. Kluwer Academic Publishers, Dordrecht 2001; b) Mandolini L., Ungaro R.: Calixarenes in Action. Imperial College Press, London 2000; c) Gutsche C. D.: Calixarenes Revisited. The Royal Society of Chemistry, Cambridge 1998; d) Vicens J., Asfari Z., Harrowfield J. M. (Eds): Calixarenes 50th Aniversary: Commemorative Issue. Kluwer Academic Publishers, Dordrecht 1994; e) Vicens J., Böhmer V. (Eds): Calixarenes: A Versatile Class of Macrocyclic Compounds. Kluwer Academic Publishers, Dordrecht 1991.
28. a) Scheerder J., Fochi M., Engbersen J. F. J., Reinhoudt D. N.: J. Org. Chem. 1994, 59, 7815;
29. b) Scheerder J., Engbersen J. F. J., Casnati A., Ungaro R., Reinhoudt D. N.: J. Org. Chem. 1995, 60, 6448;
30. c) Pelizzi N., Casnati A., Friggeri A., Ungaro R.: J. Chem. Soc., Chem. Commun. 1998, 1307;
31. d) Nam K. Ch., Kang S. O., Jeong H. S., Jeon S.: Tetrahedron Lett. 1999, 40, 7343;
32. e) Pelizzi N., Casnati A., Ungaro R.: Chem. Commun. 1998, 2607;
33. f) Casnati A., Massera C., Pelizzi N., Stibor I., Pinkhassik E., Ugozzoli F., Ungaro R.: Tetrahedron Lett. 2002, 43, 7311;
34. g) Sidorov V., Kotch F. W., Abdrakhmanova G., Mizani R., Fettinger J. C., Davis J. T.: J. Am. Chem. Soc. 2002, 124, 2267;
35. h) Tongraung P., Chantarasiri N., Tuntulani T.: Tetrahedron Lett. 2003, 44, 29.
36. a) Lin J., Hu Q. S., Xu M.-H., Pu L.: J. Am. Chem. Soc. 2002, 124, 2088;
37. b) Albrecht M., Zauner J., Burgert R., Roettele H., Froehlich R.: Mater. Sci. Eng., C 2001, 18, 185.
38. Myiano S., Nawa M., Mori A., Hashimoto H.: Bull. Chem. Soc. Jpn. 1984, 57, 2171.
39. Brueggemann R., Schmidt G.: ORTEP 3.21, PC adaptation, Ulm 1991.
40. Yabuuchi K., Marfo-Owusu E., Kato T.: Org. Biomol. Chem. 2003, 1, 3464.
41. a) Sessler J. L., Andrievsky A., Kral V., Lynch V.: J. Am. Chem. Soc. 1997, 119, 9385;
42. b) Alfonso I., Dietrich B., Robolledo F., Gotor V., Lehn J. M.: Helv. Chim. Acta 2001, 84, 280;
43. c) Rossi S., Kyne G. M., Turner D. L., Wells N. J., Kilburn J.: Angew. Chem., Int. Ed. 2002, 41, 4233.
44. Connors K. A.: Binding Constants, p. 294. Wiley, New York 1987.
45. Altomare A., Cascarano G., Giacovazzo G., Guagliardi A., Burla M. C., Polidori G., Camalli M.: SIR92 - A Program for Automatic Solution of Crystal Structures by Direct Methods. J. Appl. Crystallogr. 1994, 27, 435.
46. Watkin D. J., Prout C. K., Carruthers J. R., Betteridge P. W., Cooper R. I.: Crystals, Issue 11. Chemical Crystallography Laboratory, Oxford 2001.
47. Kývala M., Lukeš I.: Presented at Chemometrics 1995, Pardubice (Czech Republic), 1995. Book of Abstracts, p. 63 (http://www.natur. cuni.cz/~kyvala/opium.html).
48. Okada M., Mizutani M., Nishimura J.: Tetrahedron Lett. 1998, 39, 8467.
49. Gleich A., Schmidtchen F. P., Mikulcik P., Müller G.: J. Chem. Soc., Chem. Commun. 1990, 55.
50. Galán A., Andreu D., Echavarren A. M., Prados P., de Mendoza J.: J. Am. Chem. Soc. 1992, 114, 1511.