Conformation-control and stereoselective reactions using cation-π interactions

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 63, Issue 4, 2005, Pages 339-350

  Yamada, Shinji ^a  

^a OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

1, 2 dihydropyridine; 1, 4 dihydropyridine; Asymmetric acylation; Cation interaction; Conformation control; Face selective addition; Kinetic resolution; Organocatalyst; Pyridinium salt; Thiocarbonyl

Indexed keywords

AROMATIC COMPOUNDS; CATALYSTS; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; POSITIVE IONS; REACTION KINETICS; X RAY ANALYSIS;

1,4-DIHYDROPYRIDINE; ASSYMETRIC ACYLATION; FACE SELECTIVE ADDITION; KINETIC RESOLUTION; ORGANOCATALYSTS; PYRIDINIUM SALTS; THIOCARBONYL;

STEREOCHEMISTRY;

EID: 20444396583     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.63.339     Document Type: Review

References (67)

1. J. C. Ma, D. A. Dougherty, Chem. Rev., 97, 1303 (1997).
2. D. A. Stauffer, R. E. Barrans, Jr., D. A. Dougherty, Angew. Chem., Int. Ed. Engl., 29, 915 (1990)
3. J. P. Gallivan, D. A. Dougherty, Proc. Natl. Acad. Sci. U. S. A., 96, 9459 (1999);
4. N. S. Scrutton, A. R. C. Raine, Biochem. J., 319, 1 (1996)
5. B. C. Guo, J. W. Purnell, A. W. Castleman, Jr., Chem. Phys. Lett., 168, 1556 (1990)
6. G. W. Gokel, L. J. Barbour, R. Ferdani, J. Hu, Acc. Chem. Res., 35, 878 (2002)
7. G. B. Jones, Tetrahedron, 57, 7999 (2001);
8. G. B. Jones, B. J. Chapman, Synthesis, 1995, 475
9. J. Bosch, M.-L. Bennasar, Synlett, 1995, 587;
10. R. Lavilla, J. Chem. Soc., Perkin Trans. 1, 2002, 1141
11. S. Goldmann, J. Stoltefuss, Angew. Chem., Int. Ed. Engl., 30, 1559 (1991)
12. V. A. Burgess, S. G. Davies, R. T. Skerlj, Tetrahedron: Asymmetry, 2, 299 (1991)
13. (a) A. I. Meyers, T. Oppenlaender, J. Chem. Soc., Chem. Commun., 1986, 920;
14. (b) A. I. Meyers, T. Oppenlaender, idem, J. Am. Chem. Soc., 108, 1989 (1986);
15. (c) P. Mangeney, R. Gosmini, S. Raussou, M. Commerçon, A. Alexakis, J. Org. Chem., 59, 1877 (1994);
16. (d) R. Gosmini, P. Mangeney, A. Alexakis, M. Commerçon, J. -F. Normant, Synlett, 1991, 11;
17. (e) A. G. Schultz, L. Flood, J. P. Springer, J. Org. Chem., 51, 838 (1986);
18. (f) A. Ohno, S. Oda, N. Yamazaki, Tetrahedron Lett., 42, 399 (2001)
19. E. J. Corey, C.-P. Chen, G. A. Reichard, Tetrahedron Lett., 30, 5547 (1989)
20. T. Kawabata, M. Nagato, K. Takasu, K. Fuji, J. Am. Chem. Soc., 119, 3169 (1997)
21. S. Kanemasa, K. Onimura, Tetrahedron, 48, 8631 (1992)
22. S. Yamada, M. Saitoh, T. Misono, Tetrahedron Lett., 43, 5853 (2002)
23. D. E. J. E. Robinson, S. D. Bull, Tetrahedron: Asymmetry, 14, 1407 (2003)
24. (a) G. C. Fu, Ace. Chem. Res., 37, 542 (2004);
25. (b) R. Murugan, E. F. V. Scrivan, Aldrichimica Acta, 36, 21 (2003)
26. G. C. Fu, Acc. Chem. Res., 33, 412 (2000)
27. K.-S. Jeong, S.-H. Kim, H.-J. Park, K.-J. Chang, K. S. Kim, Chem. Lett., 2002, 1114
28. (a) A. C. Spivey, F. Zhu, M. B. Mitchell, S. G. Davey, R. L. Jarvest, J. Org. Chem., 68, 7379 (2003);
29. (b) G. Naraku, N. Shimomoto, T. Hanamoto, J. Inanaga, Enantiomer, 5, 135 (2000);
30. (c) G. Priem, B. Pelotier, S. J. F. Macdonald, M. S. Anson, I. B. Campbell, J. Org. Chem., 68, 3844 (2003)
31. S. Yamada, C. Morita, J. Am. Chem. Soc., 124, 8184 (2002)
32. G. H. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc., Perkin Trans. 2, 2001, 651
33. N. Berova, K. Nakanishi, "Circular Dichroism, Principles and Applications" eds. by N. Berova, K. Nakanishi, R. W. Woody, Wiley-VCH, New York, 2000, p 337
34. S. Yamada, C. Morita, J. Yamamoto, Tetrahedron Lett., 45, 7475 (2004)
35. (a) J. A. Wisner, P. D. Beer, M. G. B. Drew, Angew. Chem. Int. Ed., 40, 3606 (2001);
36. (b) D. Philip, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Chem. Soc., Chem. Commun., 1991, 1584
37. K.-y. Akiba, A. Ohtani, Y. Yamamoto, J. Org. Chem., 51, 5328 (1986)
38. J. M. White, A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc., 122, 11995 (2000)
39. R. Yamaguchi, M. Tanaka, T. Matsuda, T. Okano, T. Nagura, K. Fujita, Tetrahedron Lett., 43, 8871 (2002)
40. E. Ichikawa, M. Suzuki, K. Yabu, M. Albert, M. Kanai, M. Shibasaki, J. Am. Chem. Soc., 126, 11808 (2004)
41. R. Yamaguchi, M. Moriyasu, M. Yoshioka, M. Kawanishi, J. Org. Chem., 50, 287 (1985)
42. T-P. Loh, P-L. Lye, R-B. Wang, K-Y. Sim, Tetrahedron Lett., 41, 7779, (2000)
43. S. Kanemasa, K. Onimura, Tetrahedron, 48, 8631 (1992)
44. (a) S. Yamada, Angew. Chem., Int. Ed. Engl., 1993, 1083;
45. (b) S. Yamada, idem, J. Org. Chem., 61, 941 (1996)
46. S. Yamada, T. Misono, Tetrahedron Lett., 42, 5497 (2001)
47. S. Yamada, T. Misono, S. Tsuzuki, J. Am. Chem. Soc., 126, 9862 (2004)
48. K. Ohkata, M. Ohsugi, K. Yamamoto, M. Ohsawa, K-y. Akiba, J. Am. Chem. Soc., 118, 6355 (1996)
49. R. M. Minyaev, V. I. Minkin, Can. J. Chem., 76, 776 (1998)
50. Y. Nagao, H. Nishijima, H. Iimori, H. Ushirogochi, S. Sano, J. Shiro, J. Organometallic Chem., 611, 172 (2000)
51. C. Rovira, J. J. Novoa, Chem. Eur. J., 5, 3689 (1999)
52. S. Tsuzuki, M. Yoshida, T. Uchimaru, M. Mikami, J. Phys. Chem. A, 105, 769 (2001)
53. S. Yamada, M. Ichikawa, Tetrahedron Lett., 40, 4231 (1999)
54. S. Yamada, T. Misono, M. Ichikawa, C. Morita, Tetrahedron, 57, 8939 (2001)
55. F. Rezgui, P. Mangeney, A. Alexakis, Tetrahedron Lett., 40, 6241 (1999)
56. S. Yamada, C. Morita, Chem. Lett., 2001, 1034
57. (a) S. Yamada, T. Ohe, Tetrahedron Lett., 37, 6777 (1996);
58. (b) S. Yamada, H. Katsumata, Chem. Lett., 1998, 995;
59. (c) S. Yamada, H. Katsumata, idem, J. Org. Chem., 64, 9365 (1999);
60. (d) S. Yamada, E. Noguchi, Tetrahedron Lett., 42, 3621 (2001)
61. S. Yamada, T. Misono, Y. Iwai, Tetrahedron Lett., 46, 2239 (2005)
62. L. A. M. Bastiaansen, T. J. M. Vermeulen, H. M. Buck, W. J. J. Smeets, J. A. Kanters, A. L. Spek, J. Chem. Soc., Chem. Commun., 1988, 230