Catalytic asymmetric synthesis of quaternary carbon centers by intramolecular Heck reaction: Synthetic developments and mechanistic studies

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 58, Issue 8, 2000, Pages 718-727

  Ashimori, Atsuyuki ^a   Overman, Larry E ^b  

^a Yoshitomi Pharmaceutical Industries Ltd   (Japan)

^b NONE

Author keywords

Asymmetric synthesis; Enantioselective; Heck reaction; Intramolecular; Mechanistic studies; Palladium catalyst; Quaternary carbon center; Synthetic developments

Indexed keywords

EID: 0003374829     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.58.718     Document Type: Article

References (66)

1. (a) T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn., 44, 581 (1971);
2. (b) R. F. Heck, J. P. Nolley, Jr., J. Org. Chem., 37, 2320 (1972)
3. (a) R. F. Heck, Organic Reactions, 27, 345 (1972);
4. (b) R. F. Heck, "Comprehensive Organic Synthesis", Vol.4, ed. by B. M. Trost, Pergamon, London, 1991, p 833;
5. (c) G. D. Davies, A. Hallberg, Chem. Rev., 89, 1433 (1989);
6. (d) A. de Meijere, F. E. Meyer. Angew. Chem., Int. Ed. Engl., 33, 2379 (1994);
7. (e) S. E. Gibson, R. J. Middleton, Contemp. Org. Synth., 3, 447 (1996);
8. (f) S. Bräse, A. de Meijere, "Metal-Catalyzed Cross Coupling Reactions", eds. by P. J. Stang, F. Diederick, Wiley-VCH, Weinheim, 1998, Chapter 3;
9. (g) J. T. Link, L. E. Overman, "Metal-Catalyzed Cross Coupling Reactions", eds. by P. J. Stang, F. Diederick, Wiley-VCH, Weinheim, 1998, Chapter 6
10. (a) M. Shibasaki, "Advances in Metal-Organic Chemistry", ed. by L. S. Liebeskind, JAI, Greenwich, 1996, p 119;
11. (b) M. Shibasaki, C. D. J. Boden, A. Kojima, Tetrahedron, 53, 7371 (1997);
12. (c) M. Shibasaki, E. M. Vogl, J. Organomet. Chem., 576, 1 (1999)
13. E. J. Corey, A. Guzman-Perez, Angew. Chem., Int. Ed. Engl., 37, 388 (1998)
14. Y. Sato, M. Sodeoka, M. Shibasaki, J. Org. Chem., 54, 4738 (1989)
15. N. E. Carpenter, D. J. Kucera, L. E. Overman, J. Org. Chem., 54, 58-16 (1989)
16. W. Cabri, I. Candiani, Acc. Chem. Res., 28, 2 (1995)
17. W. Cabri, I. Candiani, S. DeBernardis, F. Francalanci, S. Penco, J. Org. Chem., 56, 5796 (1991)
18. F. Ozawa, A. Kubo, T. Hayashi, J. Am. Chem. Soc., 113, 1417 (1991)
19. F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, E. Nishioka, K. Yanagi, K. Moriguchi, Organometallics, 12, 4188 (1993)
20. T. Takemoto, M. Sodeoka, H. Sasai, M. Shibasaki, J. Am. Chem. Soc., 115, 8477 (1993)
21. (a) A. Kojima, T. Takemoto, M. Sodeoka, M. Shibasaki, J. Org. Chem., 61, 4876 (1996);
22. (b) A. Kojima, T. Takemoto, M. Sodeoka, M. Shibasaki, Synthesis, 1998, 581;
23. (c) M. Shibasaki, A. Kojima, S. Shimizu, J. Heterocyclic Chem., 35, 1057 (1998)
24. S. P. Maddaford, N. G. Andersen, W. A. Cristofoli, B. A. Keay, J. Am. Chem. Soc., 118, 10766 (1996)
25. (a) K. Kondo, M. Sodeoka, M. Shibasaki, J. Org. Chem., 60, 4322 (1995);
26. (b) K. Kondo, M. Sodeoka, M. Shibasaki, idem, Tetrahedron: Asymmetry, 6, 2453 (1995)
27. (a) K. Nakanishi, T. Goto, G. Ito, S. Natori, S. Nozoe, "Natural Products Chemistry", Vols. 1, 3, Academic Press, Inc., New York, 1974, 1983;
28. (b) M. E. Kuehne, J. A. Nelson, J. Org. Chem., 35, 161 (1970);
29. (c) R. A. Bell, R. E. Ireland, R. A. Partyka, J. Org. Chem., ibid., 27, 3741 (1962);
30. (d) C. K-F. Chiu, S. V. Govindan, P. L. Fuchs, J. Org. Chem., ibid., 59, 311 (1994)
31. (a) L. Ripa, A. Hallberg, J. Org. Chem., 62, 595 (1997);
32. (b) L. Ripa, A. Hallberg, idem, J. Org. Chem., ibid., 61, 7147 (1996)
33. (a) O. Loiseleur, M. Hayashi, N. Schmees, A. Pfaltz, Synthesis, 1997, 1338;
34. (b) O. Loiseleur, P. Meier, A. Pfaltz, Angew. Chem., Int. Ed. Engl., 35, 200 (1996)
35. S. Y. Cho, M. Shibasaki, Tetrahedron Lett., 39, 1773 (1998)
36. S. Honzawa, T. Mizutani, M. Shibasaki, Tetrahedron Lett., 40, 311 (1999)
37. P. Diaz, F. Gendre, L. Stella, B. Charpentier, Tetrahedron, 54, 4579 (1998)
38. (a) A. Ashimori, L. E. Overman, J. Org. Chem., 57, 4571 (1992);
39. (b) A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am. Chem. Soc., 120, 6477 (1998)
40. (a) A. Ashimori, B. Bachand, M. A. Calter, S. P. Govek, L. E. Overman, D. J. Poon, J. Am. Chem. Soc., 120, 6488 (1998);
41. (b) L. E. Overman, D. L. Poon, Angew. Chem., Int. Ed. Engl., 36, 518 (1997);
42. (c) A. Ashimori, T. Matsuura, L. E. Overman, D. J. Poon, J. Org. Chem., 58, 6949 (1993)
43. T. Matsuura, L. E. Overman, D. J. Poon, J. Am. Chem. Soc., 120, 6500 (1998)
44. C. R. Landis, J. Halpern, J. Am. Chem. Soc., 109, 1746 (1987)
45. (a) C. Amatore, M. Azzabi, A. Jutand, J. Am. Chem. Soc., 113, 8375 (1991);
46. (b) C. Amatore, A. Jutand, M. A. M'Barki, Organometallics, 14, 1818 (1995);
47. (c) C. Amatore, A. Jutand, A. Suarez, J. Am. Chem. Soc., 115, 9531 (1993);
48. (d) C. Amatore, G. Broeker, A. Jutand, F. Khalil, J. Am. Chem. Soc., ibid., 119, 5176 (1997)
49. J. P. Wolfe, S. Wagaw, S. L. Buchwald, J. Am. Chem. Soc., 118, 7215 (1996)
50. A. Jutand, A. Mosleh, Organometallics, 14, 1810 (1995)
51. (a) P. J. Stang, M. H. Kowalski, M. D. Schiavilli, D. Longford, J. Am. Chem. Soc., 111, 3347 (1989);
52. (b) P. J. Stang, M. H. Kowalski, J. Am. Chem. Soc., ibid., 111, 3356 (1989);
53. (c) R. J. Hinkle, P. J. Stang, M. H. Kowalski, J. Org. Chem., 55, 5033 (1990);
54. (d) J. M. Brown, K. King, Angew. Chem., Int. Ed. Engl., 35, 657 (1996)
55. J. M. Brown, J. J. Pérez-Torrente, N. W. Alcock, H. J. Clase, Organometallics, 14, 207 (1995)
56. C. Puchot, O. Samuel, E. Dunach, S. Zhao, C. Agami, H. B. Kagan, J. Am. Chem. Soc., 108, 2353 (1986)
57. (a) R. J. Cross, Adv. Inorg. Chem., 34, 219 (1989);
58. (b) M. L. Tobe, "Comprehensive Coordination Chemistry", eds. by G. Wilkinson, R. D. Gillard, J. A. McCleverty, Pergamon, Oxford, 1987, Vol. 1, p 281
59. R. Romero, Comments Inorg. Chem., 11, 21 (1990)
60. (a) V. G. Albano, C. Castellari, M. E. Cucciolito, A. Panunzi, A. Vitagliano, Organometallics, 9, 1269 (1990);
61. (b) V. G. Albano, G. Natile, A. Panunzi, Coord. Chem. Rev., 133, 67 (1994)
62. M. Portnoy, Y. Ben-David, I. Rousso, D. Milstein, Organometallics, 13, 3465 (1994)
63. A. Kojima, C. D. J. Boden, M. Shibasaki, Tetrahedron Lett., 38, 3459 (1997)
64. S. Y. W. Lau, B. A. Keay, Synlett, 1999, 605