Chiral binaphthalenes bearing two pyridine ligands attached via acetylene spacers. Synthesis and coordination study

Collection of Czechoslovak Chemical Communications

Volumn 72, Issue 8, 2007, Pages 1139-1157

  Kasák, Peter ^a,b   Brath, Henrich ^a   Krascsenicsová Poláková, Katarína ^a   Kicková, Anna ^a   Moldovan, Natalia ^a   Putala, Martin ^a  

^a Physics and Informatics   (Slovakia)

^b POLYMER INSTITUTE   (Slovakia)

Author keywords

Alkynes; Alkynylations; Biaryls; Binaphthalenes; Bispyridines; C 2 symmetric ligands; Cross coupling reactions; Helicenes; Palladium; Sonogashira reaction

Indexed keywords

EID: 34948825438     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20071139     Document Type: Article

References (43)

1. a) Connon S. J.: Angew. Chem. Int. Ed. 2006, 45, 3909;
2. b) Maruoka K., Ooi T.: Chem. Rev. 2003, 103, 3013;
3. c) Noyori R.: Asymmetric Catalysis in Organic Synthesis. Wiley, New York 1994;
4. d) Rosini C., Franzini L., Raffaelli A., Salvadori P.: Synthesis 1992, 503;
5. e) Pu L.: Chem. Rev. 1998, 98, 2405.
6. Ostroverkhov V., Petschek R. G., Singer K. D., Twieg R. J.: Chem. Phys. Lett. 2001, 340, 109.
7. a) Cram D. J.: Science 1988, 240, 760;
8. b) Telfer S. G., Kuroda R.: Coord. Chem. Rev. 2003, 242, 33; and references therein.
9. Putala M.: Enantiomer 1999, 4, 243.
10. Kasák P., Putala M.: Tetrahedron Lett. 2004, 45, 791.
11. Kasák P., Mikláš R., Putala M.: J. Organomet. Chem. 2001, 637-639, 318.
12. a) Brath H., Dubovská M., Juríček M., Kasák P., Putala M.: Collect. Czech. Chem. Commun. 2004, 69, 1517;
13. b) Kasák P., Brath H., Dubovská M., Juríček M., Putala M.: Tetrahedron Lett. 2004, 45, 791.
14. Desimoni G., Faita G., Jørgensen K. A.: Chem Rev. 2006, 106, 3561; and references therein.
15. Examples a) Pfaltz A.: Acc. Chem. Res. 1993, 26, 339;
16. b) Müller D., Umbricht G., Weber B., Pfaltz A.: Helv. Chim. Acta 1991, 74, 232.
17. Tanner D.: Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
18. Examples: a) Ito K., Katsuki T.: Tetrahedron Lett. 1993, 34, 2661;
19. b) Malkov A. V., Bella M., Langer V., Kočovský P.: Org. Lett. 2000, 2, 3047.
20. Examples: a) Gant T. G., Noe M. C., Corey E. J.: Tetrahedron Lett. 1995, 36, 8745;
21. b) Uozumi Y., Kyota H., Kishi E., Kitayama K., Hayashi T.: Tetrahedron: Asymmetry 1996, 7, 1603;
22. c) Andrus M. B., Asgari D., Sclafani J. A.: J. Org. Chem. 1997, 62, 9365;
23. d) Meyers A. I., Price A.: J. Org. Chem. 1998, 63, 412;
24. e) Bai X. L., Kang C.-Q., Liu X.-D., Gao L.-X.: Tetrahedron: Asymmetry 2005, 16, 727.
25. a) Charmant J. P. H., Fallis I. A., Hunt N. J., Lloyd-Jones G. C., Murray M., Nowak T.: J. Chem. Soc., Dalton Trans. 2000, 1723;
26. b) Charmant J. P. H., Hunt N. J., Lloyd-Jones G. C., Nowak T.: Collect. Czech. Chem. Commun. 2003, 68, 865.
27. Baidossi W., Schumann H., Blum J.: Tetrahedron 1996, 52, 8349.
28. a) An D. L., Nakano T., Orita A., Otera J.: Angew. Chem. Int. Ed. 2002, 41, 171;
29. b) Orita A., An D. L., Nakano T., Yaruva J., Ma N., Otera J.: Chem. Eur. J. 2002, 8, 2005.
30. Krascsenicsová K., Walla P., Kasák P., Uray G., Kappe O. C., Putala M.: Chem. Commun. 2004, 2606.
31. King A. O., Okukado N., Negishi E.: J. Org. Chem. 1978, 43, 358.
32. a) Walla P., Kappe O. C.: Chem. Commun. 2004, 564;
33. b) Kappe O. C.: Angew. Chem. Int. Ed. 2004, 43, 6250.
34. Harada T., Nakanishi K.: Circular Dichroism Spectroscopy - Exciton Coupling in Organic Chemistry. Oxford University Press, Oxford 1983.
35. a) Proni G., Spada G. P., Lustenberger P., Welti R., Diederich F.: J. Org. Chem. 2000, 65, 5522;
36. b) Zhou Y., Zhang D., Zhu L., Shuai Z., Zhu D.: J. Org. Chem. 2006, 71, 2123.
37. Kawano T., Shinomaru T., Ueda I.: Org. Lett. 2002, 4, 2545.
38. Komiya S.: Synthesis of Organometallic Compounds (A Practical Guide), p. 286. John Wiley & Sons, New York 1997.
39. Vondenhof M., Mattay J.: Tetrahedron Lett. 1990, 31, 985.
40. Brown K. J., Berry M. S., Murdoch J. R.: J. Org. Chem. 1985, 50, 4345.
41. Foxman B. M., Rosenblum M., Sokolov V., Khrushchova N.: Organometallics 1993, 12, 4805.
42. Sheldrick G. M.: SHELXS97: Program for Crystal Structure Solution. University of Göttingen, Göttingen 1997.
43. Sheldrick G. M.: SHELXL97. Program for Crystal Structure Refinement. University of Göttingen, Göttingen 1997.