Catalytic enantioselective synthesis of α,α-disubstituted amino acids: The strecker reaction of ketimines using chiral poly-gadolinium complexes

ACS Symposium Series

Volumn 1009, Issue , 2009, Pages 102-115

  Shibasaki, Masakatsu ^a   Kanai, Motomu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; ENANTIOSELECTIVITY; SYNTHESIS (CHEMICAL);

DIRECT METHOD; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; KETIMINES; PHARMACEUTICAL SYNTHESIS; STRECKER REACTIONS; UNNATURAL AMINO ACIDS;

AMINO ACIDS;

EID: 84874938104     PISSN: 00976156     EISSN: 19475918     Source Type: Book Series    
DOI: 10.1021/bk-2009-1009.ch007     Document Type: Conference Paper

References (32)

1. For recent reviews, see: (a) Gröger, H. Chem. Rev. 2003, 103, 2795-2828.
2. (b) Pino, C. Angew. Chem. Int. Ed. 2004, 43, 1764-1766.
3. (c) Connon, S. J. Angew. Chem. Int. Ed. 2008, 47, 1176-1178.
4. (d) Shibasaki, M.; Kanai, M.; Mita, T. Org. React. In press.
5. Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867-870.
6. Vallée reproted the catalytic enantioselective Strecker reaction of ketimines in 2000. The reported example was, however, only acetophenone-derived ketimine. See: (a) Byrne, J. J.; Chavarot, M.; Chavant, P.; Vallée, Y. Tetrahedron Lett. 2000, 41, 873-876.
7. (b) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Y. Vallée Tetrahedron Asymmetry 2001, 12, 1147-1150.
8. (a) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634-5635.
9. (b) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147-3151.
10. (c) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3153-3155.
11. (a) Becker, C.; Hoben, C.; Kunz, H. Adv. Synth. Catal. 2007, 349, 417-424.
12. (b) Blacker, J.; Clutterbuck, L. A.; Crampton, M. R.; Grosjean, C.; North, M. Tetrahedron Asymmetry 2006, 17, 1449-1456.
13. (c) Rueping, M.; Sugiono, E.; Moreth, S. A. Adv. Synth. Catal. 2007, 349, 759-764.
14. (d) Huang, J.; Liu, X.; Wen, Y.; Qin, B.; Feng, X. J. Org. Chem. 2007, 72, 204-208.
15. (e) Huang, X.; Huang, J.; Wen, Y.; Feng, X. Adv. Synth. Catal. 2006, 348, 2579-2584.
16. (f) Wang, J.; Hu, X.; Jiang, J.; Gou, S.; Huang, X.; Liu, X.; Feng, X. Angew. Chem. Int. Ed. 2007, 46, 8468-8470.
17. Riant, O.; Hannedouche, J. Org. Biomol. Chem. 2007, 5, 873-888.
18. Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908-9909.
19. For reviews, see: (a) Shibasaki, M.; Kanai, M. Org. Biomol. Chem. 2007, 5, 2027-2039.
20. (b) Shibasaki, M.; Kanai, M.; Matsunaga, S. Aldrichimica Acta 2006, 39, 31-39.
21. (b) Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491-1508.
22. Fukuda, N.; Sasaki, K.; Sastry, T. V. R. S.; Kanai, M.; Shibasaki, M. J. Org. Chem. 2006, 71, 1220-1225.
23. Sarges, R.; Howard, H. R.; Kelbaugh, P. R. J. Org. Chem. 1982, 47, 4081-4085.
24. Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116.
25. For a review, see: Shibasaki, M.; Kanai, M.; Fukuda, N. Chem. Asian J. 2007, 2, 20-38.
26. Suzuki, M.; Kato, N.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 2527-2530.
27. Kang S. H.; Jun, H.-S. Chem. Commun. 1998, 1929-1930.
28. Donohoe, T. J.; Sintim, H. O.; Sisangia L.; Harling, D. J. Angew. Chem. Int. Ed. 2004, 43, 2293-2296.
29. Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677-10678.
30. Kato, N.; Mita, T.; Kanai, M.; Therrien, B.; Kawano, M.; Yamaguchi, K.; Danjo, H.; Sei, Y.; Sato, A.; Furusho, A.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6768-6769.
31. (a) Fujimori, I.; Mita, T.; Maki, K.; Shiro, M.; Sato, A.; Furusho, S.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 16438-16439.
32. (b) Fujimori, I.; Mita, T.; Maki, K.; Shiro, M.; Sato, A.; Furusho, S.; Kanai, M.; Shibasaki, M. Tetrahedron, 2007, 63, 5820-5831.