Chiral transition metal lewis acids bearing bis(oxazolinyl)phenyl (phebox) as a princer ligand: Synthesis and application for the asymmetric reactions

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 61, Issue 4, 2003, Pages 343-351

  Motoyama, Yukihiro ^a   Nishiyama, Hisao ^b  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b NONE

Author keywords

Aldol reaction; Alkylation; Allylation; Bis(oxazolinyl)phenyl; Hetero Diels Alder reaction; Michael addition; Phebox; Pincer ligand; Transition metal lewis acid

Indexed keywords

ADDITION REACTIONS; ALDEHYDES; ALKYLATION; CATALYSTS; CONDENSATION REACTIONS; PALLADIUM; PLATINUM; RHODIUM; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

ALDOL REACTION; ALLYLATION; BIS OXAZOLINYL PHENYL; DANISHEFSKY DIENE; DIELS-ALDER REACTION; MICHAEL ADDITION; OXIDATIVE ADDITION; PINCER LIGAND; TRANSITION METAL LEWIS ACIDS; TRANSMETALLATION;

ORGANIC COMPOUNDS;

EID: 0037937530     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.61.343     Document Type: Article

References (57)

1. (a) H. B. Kagan, O. Riant, Chem. Rev., 92, 1007 (1992)
2. (b) (1995), p. 177
3. (a) B. Bosnich, Aldrichimica Acta, 31, 76, (1998)
4. (b) Ed. H. Yamamoto, "Lewis Acid Reagents: A Practical Approach", Oxford U. P., UK (1999)
5. (c) Ed., H. Yamamoto, "Lewis Acids in Organic Synthesis", Wiley-VCH Verlag GmbH, Weinheim (2000)
6. Y. Motoyama, H. Nishiyama, "Latest Frontiers of Organic Synthesis": Ed., Y. Kobayashi, Research Signpost, India (2002), p 1
7. Y. Motoyama, N. Makihara, Y. Mikami, K. Aoki, H. Nishiyama, Chem. Lett., 1997, 951
8. (a) Y. Motoyama, H. Narusawa, H. Nishiyama, Chem. Commun., 1999, 131
9. (b) Y. Motoyama, M. Okano, H. Narusawa, N. Makihara, K. Aoki, H. Nishiyama, Organometallics, 20, 1580 (2001)
10. (a) 53, 500 (1995)
11. (b) H. Nishiyama, "Advances in Catalytic Processes": Ed., M. P. Doyle, JAI Press Inc., New York (1997), vol. 2, p 153
12. (c) H. Nishiyama, Enantiomer, 4, 569 (1999)
13. (a) H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics, 10, 500 (1991)
14. (b) R. Nesper, P. Pregosin, K. Puntener, M. Worle, A. Albinati, J. Organomet. Chem., 507, 85 (1996)
15. C. L. Moulton, B. L. Shaw, J. Chem. Soc., Dalton Trans., 1976, 1020
16. (a) M. H. P. Rietveld, D. M. Grove, G. van Koten, New J. Chem., 21, 751, (1997)
17. (b) R. A. Gossage, L. A. van de Kuil, G. van Koten, Acc. Chem. Res., 31, 423 (1998)
18. (c) B. Rybtchinski, D. Milstein, Angew. Chem., Int. Ed., 38, 870 (1999)
19. (d) C. M. Jensen, Chem. Commun., 1999, 2443
20. (e) A. Vigalok, D. Milstein, Acc. Chem. Res., 34, 798 (2001)
21. (f) M. Albrecht, G. van Koten, Angew. Chem., Int. Ed., 40, 3751 (2001)
22. (g) B. S. Williams, P. Dani, M. Lutz, A. L. Spek, G. van Koten, Helv. Chim. Acta, 84, 3519 (2001)
23. (a) L. A. van de Kuil, Y. S. J. Veldhuizen, D. M. Grove, J. W. Zwikker, L. W. Jenneskens, W. Drenth, W. J. S. Smeets, A. L. Spek, G. van Koten, Recl. Trav. Chim. Pay-Bas, 113, 267 (1994)
24. (b) F. Gorla, A. Togni, L. M. Venanzi, A. Albinati, F. Lianza, Organometallics, 13, 1607 (1994)
25. (c) J. M. Longmire, X. Zhang, M. Shang, ibid., 17, 4374 (1998)
26. (d) M. Albrecht, B. M. Kocks, A. L. Spek, G. van Koten, J. Organomet. Chem., 624, 271 (2001)
27. H. Nishiyama, M. Kondo, T. Nakamura, K. Itoh, Organometallics, 10, 500 (1991)
28. Y. Motoyama, Y. Koga, K. Kobayashi, K. Aoki, H. Nishiyama, Chem. Eur. J., 8, 2968 (2002)
29. Y. Motoyama, Y. Koga, H. Nishiyama, Tetrahedron, 57, 853 (2001)
30. Y. Motoyama, K. Shimozono, K. Aoki, H. Nishiyama
31. (a) Y. Motoyama, Y. Mikami, H. Kawakami, K. Aoki, H. Nishiyama, Organometallics, 18, 3584 (1999)
32. (b) Y. Motoyama, H. Kawakami, K. Shimozono, K. Aoki, H. Nishiyama, ibid., 21, 3408 (2002)
33. J. Terheijden, G. van Koten, J. L. de Booys, H. J. C. Ubbels, C. H. Stram, Organometallics, 2, 1882 (1983)
34. (a) Y. Motoyama, H. Nishiyama
35. (b) 1 G4-43 (2002)
36. (a) U. S. Racherla, Y. Liao, H. C. Brown, J. Org. Chem., 57, 6614 (1992)
37. (b) S. E. Denmark, D. M. Coe, N. E. Pratt, B. D. Griedel, J. Org. Chem., 59, 6161 (1994)
38. (c) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, A. Umani-Ronchi, J. Am. Chem. Soc., 115, 7001 (1993)
39. (a) S. J. Danishefsky, E. Larson, D. Askin, N. Kato, J. Am. Chem. Soc., 107, 246 (1985)
40. (b) S. J. Danishefsky, G. G. Selnick, R. E. Zelle, M. P. Deninno, J. Am. Chem. Soc., 110, 4368 (1988)
41. (c) M. A. McCarrick, Y.-D. Wu, K. N. Houk, J. Org. Chem., 58, 3330 (1993)
42. J. J. P. Stewart, MOPAC 2002 Version 1.00, Fujitsu Limited, Tokyo Japan, 2002
43. (a) M. T. Reetz, M. Hullmann, W. Massa, S. Berger, P. Radenmacher, P. Heymanns, J. Am. Chem. Soc., 108, 2405 (1986)
44. (b) E. J. Corey, T.-P. Loh, S. Sarsher, M. D. Azimioara, Tetrahedron Lett., 33, 6945 (1992)
45. (c) E. J. Corey, J. J. Rohde, A. Fischer, M. D. Azimioara ibid., 38, 33 (1997)
46. (d) E. J. Corey, T. W. Lee, Chem. Commun., 2001 1321
47. K. Soai, T. Shibata, Comprehensive Asymmetric Catalysis, E. N. Jacobsen, A. Phaltz, H. Yamamoto, Eds., Springer-Verlag, Berlin (1999), Chapter 26.1, p 911
48. G. A. Stark, J. A. Galdysz, Inorg. Chim. Acta, 269, 167 (1998)
49. (a) I. Ugi, Isonitrile Chemistry, Academic Press, New York (1971)
50. (b) D. Hoppe, Angew. Chem., Int. Ed. Engl., 13, 789 (1974)
51. (c) U. Schöllkopf, F. Gerhart, ibid., 16, 339 (1977)
52. Y. Motoyama, K. Shimozono, K. Aoki, H. Nishiyama, Organometallics, 21, 1684 (2002)
53. J. Long, J. Hu, X. Shen, B. Ji, K. Ding, J. Am. Chem. Soc., 124, 10 (2002)
54. (a) S. E. Denmark, R. A. Stavenger A.-M. Faucher, J. P. Edwards, J. Org. Chem., 62, 3375 (1997)
55. (b) M. A. Stark, C. J. Richards, Tetrahedron Lett., 38, 5881 (1997)
56. (c) M. A. Stark, G. Jones, C. J. Richards, Organometallics, 19, 1282 (2000)
57. (d) M. Gerisch, J. R. Krumper, R. G. Bergman, T. D. Tilley, J. Am. Chem. Soc., 123, 5818 (2001)