Dienyl homoallyl alcohols via palladium catalyzed ene-type reaction of aldehydes with 1,3-dienes

Journal of the American Chemical Society

Volumn 132, Issue 46, 2010, Pages 16346-16348

  Fukushima, Masahiro ^a   Takushima, Daiki ^a   Kimura, Masanari ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLATIONS; C-C DOUBLE BONDS; CONJUGATED DIENES; ELECTRON DENSITIES; HOMOALLYL ALCOHOL; PD CATALYST; XANTPHOS;

ALDEHYDES; PALLADIUM;

OLEFINS;

ALCOHOL DERIVATIVE; ALDEHYDE; DIENYL HOMOALLYL ALCOHOL; PALLADIUM; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION;

EID: 78649288842     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1072417     Document Type: Article

References (49)

1. Hao, J., Hatano, M., and Mikami, K. Org. Lett. 2000, 2, 4059
2. Hatano, M., Terada, M., and Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249
3. Becker, J. J., Van Orden, L. J., White, P. S., and Gagné, M. R. Org. Lett. 2002, 4, 727
4. Aikawa, K., Kainuma, S., Hatano, M., and Mikami, K. Tetrahedron Lett. 2004, 45, 183
5. Mikami, K., Aikawa, K., Kainuma, S., Kawakami, Y., Saito, T., Sayo, N., and Kumobayashi, H. Tetrahedron: Asymmetry 2004, 15, 3885
6. Doherty, S., Knight, J. G., Smyth, C. H., Harrington, R. W., and Clegg, W. J. Org. Chem. 2006, 71, 9751
7. Luo, H.-K., Khim, L. B., Schumann, H., Lim, C., Jie, T. X., and Yang, H.-Y. Adv. Synth. Catal. 2007, 349, 1781
8. Zheng, K., Shi, J., Liu, X., and Feng, X. J. Am. Chem. Soc. 2008, 130, 15770
9. Ho, C.-Y., Schleicher, K. D., Chan, C.-W., and Jamison, T. F. Synlett 2009, 2549
10. Yang, N. C., Yang, D.-D. H., and Ross, C. B. J. Am. Chem. Soc. 1959, 81, 133
11. Blomquist, A. T. and Himics, R. J. J. Org. Chem. 1968, 33, 1156
12. Snider, B. B. and Rodini, D. J. Tetrahedron Lett. 1980, 21, 1815
13. Snider, B. B., Rodini, D. J., Kirk, T. C., and Cordova, R. J. Am. Chem. Soc. 1982, 104, 555
14. Cartaya-Marin, C. P., Jackson, A. C., and Snider, B. B. J. Org. Chem. 1984, 49, 2443
15. Brown, H. C. and Randad, R. S. Tetrahedron 1990, 46, 4463
16. Yu, C.-M., Jeon, M., Lee, J.-Y., and Jeon, J. Eur. J. Org. Chem. 2001, 1143
17. Sato, Y., Takimoto, M., and Mori, M. J. Am. Chem. 2000, 122, 1624
18. Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, 2005.
19. Metal Catalyzed Reductive C-C Bond Formation; Krische, M. J., Ed.; Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 2007; Vol. 279.
20. Jang, H.-Y., Huddleston, R. R., and Krische, M. J. Angew. Chem., Int. Ed. 2003, 42, 4074
21. Bower, J. F., Patman, R. L., and Krische, M. J. Org. Lett. 2008, 10, 1033
22. Shibahara, F., Bower, J. F., and Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6338
23. Smejkal, T., Han, H., Breit, B., and Krische, M. J. J. Am. Chem. Soc. 2009, 131, 10366
24. Kimura, M., Ezoe, A., Shibata, K., and Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033
25. Kimura, M., Fujimatsu, H., Ezoe, A., Shibata, K., Shimizu, M., Matsumoto, S., and Tamaru, Y. Angew. Chem., Int. Ed. 1999, 38, 397
26. Shibata, K., Kimura, M., Shimizu, M., and Tamaru, Y. Org. Lett. 2001, 3, 2181
27. Kimura, M., Ezoe, A., Tanaka, S., and Tamaru, Y. Angew. Chem., Int. Ed. 2001, 40, 3600
28. Kimura, M., Miyachi, A., Kojima, K., Tanaka, S., and Tamaru, Y. J. Am. Chem. Soc. 2004, 126, 14360
29. Kimura, M., Ezoe, A., Mori, M., Iwata, K., and Tamaru, Y. J. Am. Chem. Soc. 2006, 128, 8559
30. Kimura, M., Nojiri, D., Fukushima, M., Oi, S., Sonoda, Y., and Inoue, Y. Org. Lett. 2009, 11, 3794
31. Yin, J. and Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043
32. Ney, J. E. and Wolfe, J. P. J. Am. Chem. Soc. 2005, 127, 8644
33. Johns, A. M., Utsunomiya, M., Incarvito, C. D., and Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 1828
34. Fujita, K., Yamashita, M., Puschmann, F., Alvarez-Falcon, M. M., Incarvito, C. D., and Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 9044
35. Grushin, V. V. and Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 12644
36. Johns, A. M., Liu, Z., and Hartwig, J. F. Angew. Chem., Int. Ed. 2007, 46, 7259
37. Mora, G., Deschamps, B., Zutphen, S., Goff, X. F. L., Ricard, L., and Floch, P. L. Organometallics 2007, 26, 1846
38. Bravo-Altamirano, K., Abrunhosa-Thomas, I., and Montchamp, J.-L. J. Org. Chem. 2008, 73, 2292
39. Sun, C. and Xu, B. J. Org. Chem. 2008, 73, 7361
40. Suto, Y., Yamagiwa, N., and Torisawa, Y. Tetrahedron Lett. 2008, 49, 5732
41. López-Pérez, A., Adrio, J., and Carretero, J. C. Org. Lett. 2009, 11, 5541
42. Ohshima, T., Miyamoto, Y., Ipposhi, J., Nakahara, Y., Utsunomiya, M., and Mashima, K. J. Org. Chem. 2009, 131, 14317
43. 1,3-Pentadiene was not adequate for the reaction, and an intractable mixture was obtained.
44. Krishna, P. R., Narsingam, M., Reddy, P. S., Srinivasulu, G., and Kunwar, A. C. Tetrahedron Lett. 2005, 46, 8885
45. When 1-hexene or α-methylstyrene was used in place of conjugated diene under similar conditions, no reaction took place at all. These results rule out the present reaction proceeds via the typical carbonyl ene reaction mechanism.
46. Gillie, A. and Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933
47. Leeuwen, P. W. N. M., Kamer, P. C. j., Reek, J. N. H., and Dierkes, P. Chem. Rev 2000, 100, 2741
48. Fujihara, T., Katafuchi, Y., Iwai, T., Terao, J., and Tsuji, Y. J. Am. Chem. Soc. 2010, 132, 2094
49. Stereoselective formation of (2 E,4 E)- 1e might be executed by endo β-hydride elimination of anti -4-methoxycarbonyl-3-phenyl-2- oxapalladacyclopentane, which is prepared from a mixture of Pd/Xantphos, methyl sorbate, and benzaldehyde (entry 4 in Table 2).