New efficient method for the synthesis of chiral 2,2′-bipyridyl ligands

Synthesis

Volumn , Issue 13, 2005, Pages 2176-2182

  Ishikawa, Shunpei ^a   Hamada, Tomoaki ^a   Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric reduction; Catalyst; Chiral 2,2 bipyridine; Chiral ligand; Homo coupling

Indexed keywords

CATALYSTS; REDUCTION; SYNTHESIS (CHEMICAL);

ASYMMETRIC REDUCTION; CHIRAL 2,2′-BIPYRIDINE; CHIRAL LIGAND; HOMO-COUPLING;

ORGANIC COMPOUNDS;

2,2' BIPYRIDINE; 2,6 DIBROMOPYRIDINE; LIGAND; METAL; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; REDUCTION KINETICS; SYNTHESIS;

EID: 23944488886     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869983     Document Type: Article

References (30)

1. Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
2. (a) Constable, E. C. Adv. Inorg. Chem. 1989, 34, 1.
3. (b) McKenzie, D. E. Coord. Chem. Rev. 1971, 6, 187.
4. (c) McWhinnie, W. R.; Miller, J. D. Adv. Inorg. Chem. Radiochem. 1969, 12, 135.
5. (a) Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 205.
6. (b) Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G. Chem. Ber. 1992, 125, 1169.
7. (a) Bolm, C.; Schlingloff, G.; Harms, K. Chem. Ber. 1992, 125, 1191.
8. (b) Bolm, C.; Ewald, M. Tetrahedron Lett. 1990, 31, 5011.
9. (c) Bolm, C.; Ewald, M.; Felder, M. Chem. Ber. 1992, 125, 1205.
10. (d) Kwong, H.-L.; Lee, W.-S.; Ng, H.-F.; Chiu, W.-H.; Wong, W.-T. J. Chem. Soc., Dalton Trans. 1998, 1043.
11. (e) Kwong, H.-L.; Lau, K.-M.; Lee, W.-S.; Wong, W.-T. New J. Chem. 1999, 23, 629.
12. Ishikawa, S.; Hamada, T.; Manabe, K.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 12236.
13. Schneider, C.; Shreekanth, A. R.; Mai, E. Angew. Chem. Int. Ed. 2004, 43, 5691.
14. (a) Chandrasekharan, J.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1985, 50, 5446.
15. (b) Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Org. Chem. 1986, 51, 3394.
16. (c) Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Am. Chem. Soc. 1988, 110, 1539.
17. Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Montanucci, M. Synthesis 1984, 736.
18. (a) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
19. (b) Okano, K.; Murata, K.; Ikariya, T. Tetrahedron Lett. 2000, 41, 9277.
20. (a) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
21. (b) Noyori, R.; Ohkuma, T. Angew. Chem. Int. Ed. 2001, 40, 40.
22. Kuroboshi, M.; Waki, Y.; Tanaka, H. Synlett 2002, 637.
23. Ohkuma, T.; Koizumi, M.; Yoshida, M.; Noyori, R. Org. Lett. 2000, 2, 1749.
24. (a) Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573.
25. (b) Weingarten, H.; White, W. A. J. Org. Chem. 1966, 31, 3427.
26. (a) Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
27. (b) Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U.-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461.
28. Reger, D. L.; Gardinier, J. R.; Smith, M. D.; Pellechia, P. J. Inorg. Chem. 2003, 42, 482.
29. Vögtle, F.; Neumann, U. Chem. Ber. 1989, 122, 589.
30. The structural data of the camphanate derived from 10 and 11 have been deposited at the Cambridge Crystallographic Data Centre under the reference numbers CCDC 262163, 262164, respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 union Road, Cambridge CB2 1EZ, UK [Fax: +44 1223 336033; E-mail: deposit@ccdc.cam.ac.uk].