Rhodium-catalyzed asymmetric addition of aryl- and alkenylboron reagents to electron-deficient olefins

Pure and Applied Chemistry

Volumn 76, Issue 3, 2004, Pages 465-475

  Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AMIDE; BORON DERIVATIVE; KETONE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; RHODIUM;

ADDITION REACTION; ARYLATION; CATALYSIS; CONFERENCE PAPER; ELECTRON; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 2442671917     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200476030465     Document Type: Conference Paper

References (63)

1. (a) I. Ojima. Catalytic Asymmetric Synthesis II, Wiley-VCH, New York (2000);
2. (b) E. N. Jacobsen, A. Pfaltz, H. Yamamoto. Comprehensive Asymmetric Catalysis, Vols. 1-3, Springer, Berlin (1999);
3. (c) R. Noyori. Asymmetric Catalysis in Organic Synthesis, John Wiley, New York (1994).
4. For reviews on 1,4-addition reactions: (a) P. Perlmutter. Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford (1992);
5. (b) H.-G. Schmalz. In Comprehensive Organic Synthesis, B. M. Trost and I. Fleming, (Eds.), Vol. 4, Chap. 1.5, Pergamon, Oxford (1991);
6. (c) B. E. Rossiter and N. M. Swingle. Chem. Rev. 92, 771 (1992).
7. For recent reviews on catalytic asymmetric 1,4-addition: (a) N. Krause and A. Hoffmann-Röder. Synthesis 171 (2001);
8. (b) M. P. Sibi and S. Manyem. Tetrahedron 56, 8033 (2000);
9. (c) K. Tomioka and Y. Nagaoka. In Comprehensive Asymmetric Catalysis, E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds.), Vol. 3, Chap. 31.1, Springer, Berlin (1999);
10. (d) M. Kanai and M. Shibasaki. In Catalytic Asymmetric Synthesis, 2nd ed., I. Ojima (Ed.), pp. 569-592, John Wiley, New York (2000).
11. As examples of the copper-catalyzed asymmetric 1,4-addition of organozinc reagents generating zinc enolates: (a) H. Mizutani, S. J. Degrado, A. H. Hoveyda. J. Am. Chem. Soc. 124, 779 (2002);
12. (b) A. Alexakis, C. Benhaim, S. Rosset, M. Humam. J. Am. Chem. Soc. 124, 5262 (2002);
13. (c) L. A. Arnold, R. Naasz, A. J. Minnaard, B. L. Feringa. J. Am. Chem. Soc. 123, 5841 (2001);
14. (d) A. Alexakis, G. P. Trevitt, G. Bernardinelli. J. Am. Chem. Soc. 123, 4358 (2001);
15. (e) S. J. Degrado, H. Mizutani, A. H. Hoveyda. J. Am. Chem. Soc. 123, 755 (2001);
16. (f) I. H. Escher and A. Pfaltz. Tetrahedron 56, 2879 (2000);
17. (g) M. Yan and A. S. C. Chan. Tetrahedron Lett. 40, 6645 (1999).
18. For examples for catalytic asymmetric Michael addition of malonate esters, see: (a) M. Yamaguchi, T. Shiraishi, M. Hirama. J. Org. Chem. 61, 3520 (1996);
19. (b) T. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki. Angew. Chem., Int. Ed. Engl. 35, 104 (1996);
20. (c) M. Shibasaki, H. Sasai, T. Arai. Angew. Chem., Int. Ed. Engl. 36, 1236 (1997);
21. (d) Y. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki. J. Am. Chem. Soc. 122, 6506 (2000), and references cited therein.
22. M. Sakai, H. Hayashi, N. Miyaura. Organometallics 16, 4229 (1997).
23. Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura. J. Am. Chem. Soc. 120, 5579 (1998).
24. (a) M. Kuriyama, K. Nagai, K. Yamada, Y. Miwa, T. Taga, K. Tomioka. J. Am. Chem. Soc. 124, 8932 (2002);
25. (b) M. T. Reetz, D. Moulin, A. Gosberg. Org. Lett. 3, 4083 (2001);
26. (c) R. Amengual, V. Michelet, J.-P. Genêt. Synlett 1791 (2002);
27. (d) J.-G. Boiteau, R. Imbos, A. J. Minnaard, B. L. Feringa. Org. Lett. 5, 681 (2003).
28. For reviews concerned with the rhodium-catalyzed asymmetric addition: (a) K. Fagnou and M. Lautens. Chem. Rev. 103, 169 (2003);
29. (b) T. Hayashi and K. Yamasaki. Chem. Rev. 103, 2829 (2003);
30. (c) C. Bolm, J. P. Hildebrand, K. Muniz, N. Hermanns. Angew. Chem., Int. Ed. Engl. 40, 3284 (2001);
31. (d) T. Hayashi. Synlett 879 (2001).
32. T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara. Org. Synth. 79, 84 (2002).
33. Y. Takaya, M. Ogasawara, T. Hayashi. Tetrahedron Lett. 39, 8479 (1998).
34. Y. Takaya, M. Ogasawara, T. Hayashi. Tetrahedron Lett. 40, 6957 (1999).
35. Y. Takaya, T. Senda, H. Kurushima, M. Ogasawara, T. Hayashi. Tetrahedron: Asymmetry 10, 4047 (1999).
36. S. Sakuma, M. Sakai, R. Itooka, N. Miyaura. J. Org. Chem. 65, 5951 (2000).
37. S. Sakuma and N. Miyaura. J. Org. Chem. 66, 8944 (2001).
38. T. Senda, M. Ogasawara, T. Hayashi. J. Org. Chem. 66, 6852 (2001).
39. T. Hayashi, T. Senda, Y. Takaya, M. Ogasawara. J. Am. Chem. Soc. 121, 11591 (1999).
40. Y. Tokunaga, H. Ueno, Y. Shimomura, T. Seo. Heterocycles 57, 787 (2002).
41. T. Hayashi, T. Senda, M. Ogasawara. J. Am. Chem. Soc. 122, 10716 (2000).
42. T. Hayashi, M. Takahashi, Y. Takaya, M. Ogasawara. J. Am. Chem. Soc. 124, 5052 (2002).
43. F. Ozawa, A. Kubo, Y. Matsumoto, T. Hayashi, E. Nishioka, K. Yanagi, K. Moriguchi. Organometallics 12, 4188 (1993), and references cited therein.
44. (a) M. Sakai, M. Ueda, N. Miyaura. Angew. Chem., Int. Ed. Engl. 37, 3279 (1998);
45. (b) M. Ueda and N. Miyaura. J. Org. Chem. 65, 4450 (2000).
46. M. Ueda and N. Miyaura. J. Organomet. Chem. 595, 31 (2000).
47. K. Oguma, M. Miura, T. Satoh, M. Nomura. J. Am. Chem. Soc. 122, 10464 (2000).
48. (a) M. Lautens, C. Dockendorff, K. Fagnou, A. Malicki. Org. Lett. 4, 1311 (2002);
49. (b) M. Lautens, K. Fagnou, S. Hiebert. Acc. Chem. Res. 36, 48 (2003).
50. (a) S. Oi, M. Moro, S. Ono, Y. Inoue. Chem. Lett. 83 (1998);
51. (b) S. Oi, M. Moro, H. Ito, Y. Honma, S. Miyano, Y. Inoue. Tetrahedron 58, 91 (2002);
52. (c) T.-S. Huang and C.-J. Li. Org. Lett. 3, 2037 (2001);
53. (d) S. Venkatraman, Y. Meng, C.-J. Li. Tetrahedron Lett. 42, 4459 (2001).
54. (a) S. Oi, Y. Honma, Y. Inoue. Org. Lett. 4, 667 (2002);
55. (b) S. Oi, M. Moro, Y. Inoue. Organometallics 20, 1036 (2001);
56. (c) A. Mori, Y. Danda, T. Fujii, K. Hirabayashi, K. Osakada. J. Am. Chem. Soc. 123, 10774 (2001);
57. (d) T. Koike, X. Du, A. Mori, K. Osakada. Synlett 301 (2002);
58. (e) A. Mori and T. Kato. Synlett 1167 (2002).
59. S. Venkatraman and C.-J. Li. Tetrahedron Lett. 42, 781 (2002).
60. S. Oi, A. Taira, Y. Honma, Y. Inoue. Org. Lett. 5, 97 (2003).
61. (a) T. Hayashi and M. Ishigedani. J. Am. Chem. Soc. 122, 976 (2000);
62. (b) T. Hayashi and M. Ishigedani. Tetrahedron 57, 2589 (2001).
63. T. Hayashi, N. Tokunaga, K. Yoshida, J. W. Han. J. Am. Chem. Soc. 124, 12102 (2002).