Asymmetric 1,4-addition of triarylbismuths to enones catalyzed by dicationic palladium(II) complexes

Chemical Communications

Volumn , Issue 16, 2004, Pages 1822-1823

  Nishikata, Takashi ^a   Yamamoto, Yasunori ^a   Miyaura, Norio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BISMUTH DERIVATIVE; CARBONYL DERIVATIVE; DICATIONIC PALLADIUM COMPLEX; METHANOL; ORGANOBORON DERIVATIVE; ORGANOSILICON DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; RHODIUM COMPLEX; TITANIUM DERIVATIVE; TRIARYLBISMUTH; UNCLASSIFIED DRUG; ZINC DERIVATIVE; ZIRCONIUM DERIVATIVE;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY;

EID: 4644334182     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b407272c     Document Type: Article

References (40)

1. M. Sakai, H. Hayashi and N. Miyaura, Organometallics, 1997, 16, 4229.
2. (a) Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai and N. Miyaura, J. Am. Chem. Soc., 1998, 120, 5579;
3. (b) T. Hayashi, T. Senda, Y. Takaya and M. Ogasawara, J. Am. Chem. Soc., 1999, 121, 11591;
4. (c) T. Hayashi, T. Senda and M. Ogasawara, J. Am. Chem. Soc., 2000, 122, 10716;
5. (d) S. Sakuma and N. Miyaura, J. Org. Chem., 2001, 66, 8944;
6. (e) S. Sakuma, M. Sakai, R. Itooka and N. Miyaura, J. Org. Chem., 2000, 65, 5951;
7. (f) M. Reetz, D. Moulin and A. Gosberg, Org. Lett., 2001, 3, 4083;
8. (g) M. Kuriyama, K. Nagai, K. Yamada, Y. Miwa, T. Taga and T. Tomioka, J. Am. Chem. Soc., 2002, 124, 8932;
9. (h) K. Yoshida, M. Ogasawara and T. Hayashi, J. Am. Chem. Soc., 2002, 124, 10984;
10. (i) T. Hayashi, M. Takahashi, Y. Tkaya and M. Ogasawara, J. Am. Chem. Soc., 2002, 124, 5052;
11. (j) M. Pucheault, S. Darses and J.-P. Genet, Tetrahedron Lett., 2002, 43, 6157;
12. (k) T. Hayashi, K. Ueyama, N. Tokunaga and K. Yoshida, J. Am. Chem. Soc., 2003, 125, 11508;
13. (l) Y. Ma, C. Song, C. Ma, Z. Sun, Q. Chai and M. B. Andrus, Angew. Chem., Int. Ed., 2003, 42, 5871;
14. (m) J.-G. Boiteau, R. Imbos, A. J. Minnaard and B. L. Feringa, Org. Lett., 2003, 5, 681;
15. (n) J.-M. Boiteau, A. J. Minnaard and B. L. Feringa, J. Org. Chem., 2003, 68, 9481.
16. (a) M. Murata, R. Shimazaki, M. Ishikura, S. Watanabe and Y. Masuda, Synthesis, 2002, 717;
17. (b) T. Koike, X. Du, A. Mori and K. Osakada, Synlett, 2002, 301;
18. (c) S. Oi, Y. Honma and Y. Inoue, Org. Lett., 2002, 4, 667;
19. (d) T.-S. Huang and C.-J. Li, Chem. Commun., 2001, 2348;
20. (e) S. Oi, A. Taira, Y. Honma and Y. Inoue, Org. Lett., 2003, 5, 97.
21. (a) S. Venkatraman and C.-J. Li, Tetrahedron Lett., 2001, 42, 781;
22. (b) T. Huang, Y. Meng, S. Venkatraman, D. Wang and C.-J. Li, J. Am. Chem. Soc., 2001, 123, 7451.
23. (a) S. Oi, M. Moro, S. Ono and Y. Inoue, Chem. Lett., 1998, 83;
24. (b) S. Venkatraman, Y. Meng and C.-J. Li, Tetrahedron Lett., 2001, 42, 4459;
25. (c) T.-S. Huang and C.-J. Li, Org. Lett., 2001, 3, 2037;
26. (d) S. Oi, M. Moro, H. Ito, Y. Honma, S. Miyano and Y. Inoue, Tetrahedron, 2002, 58, 91.
27. (a) T. Hayashi, N. Tokunaga, K. Yoshida and J. W. Han, J. Am. Chem. Soc., 2002, 124, 12102;
28. (b) K. Yoshida and T. Hayashi, J. Am. Chem. Soc., 2003, 125, 2872.
29. A. Kakuuchi, T. Taguchi and Y. Hanzawa, Tetrahedron, 2004, 60, 1293.
30. R. Shintani, N. Tokunaga, H. Doi and T. Hayashi, J. Am. Chem. Soc., 2004, 126, 6240.
31. (a) T. Hayashi and K. Yamasaki, Chem. Rev., 2003, 103, 2829;
32. (b) K. Fagnou and M. Lautens, Chem. Rev., 2003, 103, 169;
33. (c) N. Krause and A. Hoffmann-Röder, Synthesis, 2001, 171.
34. T. Nishikata, Y. Yamamoto and N. Miyaura, Angew. Chem., Int. Ed., 2003, 42, 2768.
35. T. Nishikata, Y. Yamamoto and N. Miyaura, Chem. Lett., 2003, 32, 752.
36. (a) H. Gilman and H. L. Yale, Chem. Rev., 1942, 30, 281.
37. Pd-catalyzed reactions of Bi (b) M. L. N. Rao, S. Shimada, O. Yamazaki and M. Tanaka, J. Organomet. Chem., 2002, 659, 117; (c) M. L. N. Rao, O. Yamazaki, S. Shimada, T. Tanaka, Y. Suzuki and M. Tanaka, Org. Lett., 2001, 3, 4103; (d) M. L. N. Rao, S. Shimada and M. Tanaka, Org. Lett., 1999, 1, 1271; (e) D. H. R. Barton, N. Ozbalik and M. Ramesh, Tetrahedron, 1988, 44, 5661.
38. Pd-catalyzed reactions of Bi (b) M. L. N. Rao, S. Shimada, O. Yamazaki and M. Tanaka, J. Organomet. Chem., 2002, 659, 117; (c) M. L. N. Rao, O. Yamazaki, S. Shimada, T. Tanaka, Y. Suzuki and M. Tanaka, Org. Lett., 2001, 3, 4103; (d) M. L. N. Rao, S. Shimada and M. Tanaka, Org. Lett., 1999, 1, 1271; (e) D. H. R. Barton, N. Ozbalik and M. Ramesh, Tetrahedron, 1988, 44, 5661.
39. Pd-catalyzed reactions of Bi (b) M. L. N. Rao, S. Shimada, O. Yamazaki and M. Tanaka, J. Organomet. Chem., 2002, 659, 117; (c) M. L. N. Rao, O. Yamazaki, S. Shimada, T. Tanaka, Y. Suzuki and M. Tanaka, Org. Lett., 2001, 3, 4103; (d) M. L. N. Rao, S. Shimada and M. Tanaka, Org. Lett., 1999, 1, 1271; (e) D. H. R. Barton, N. Ozbalik and M. Ramesh, Tetrahedron, 1988, 44, 5661.
40. Pd-catalyzed reactions of Bi (b) M. L. N. Rao, S. Shimada, O. Yamazaki and M. Tanaka, J. Organomet. Chem., 2002, 659, 117; (c) M. L. N. Rao, O. Yamazaki, S. Shimada, T. Tanaka, Y. Suzuki and M. Tanaka, Org. Lett., 2001, 3, 4103; (d) M. L. N. Rao, S. Shimada and M. Tanaka, Org. Lett., 1999, 1, 1271; (e) D. H. R. Barton, N. Ozbalik and M. Ramesh, Tetrahedron, 1988, 44, 5661.