Catalytic enantioselective Michael addition of 1,3-dicarbonyl compounds to nitroalkenes catalyzed by well-defined chiral Ru amido complexes

Journal of the American Chemical Society

Volumn 126, Issue 36, 2004, Pages 11148-11149

  Watanabe, Masahito ^a   Ikagawa, Ayako ^a   Wang, Hui ^a   Murata, Kunihiko ^a   Ikariya, Takao ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DICARBONYL DERIVATIVE; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; MICHAEL ADDITION;

EID: 4544301719     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046296g     Document Type: Article

References (37)

1. Recent leading reviews of asymmetric Michael addition to nitroalkenes: (a) Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
2. (b) Kranse, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
3. Cu-catalyzed 1,4-addition of diethylzine: (a) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341.
4. (b) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579.
5. (c) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773.
6. (d) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003. 125, 3700.
7. (e) Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192.
8. Ti catalysts: Schäfer, H. S.; Seebach, D. Tetrahedron 1995, 51, 2305.
9. Mg catalysts: (a) Jianguo, Ji.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215.
10. (b) Barnes, D. M.; Ji, J.; Fickes, M. G.; Fitzgerald, M. A.; King, S. A.; Morton, H. E.; Plagge, F. A.; Preskill, M.; Wagaw, S. H.; Wittenberger, S. J.; Zhang, J. J. Am. Chem. Soc. 2002, 124, 13097.
11. Rh catalysts: Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716.
12. Organocatalysts: (a) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257.
13. (b) Alexakis, A.; Andrey, O. Org. Lett. 2002, 4, 3611.
14. (c) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
15. (d) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559.
16. (e) Brunner, H.; Kimel, B. Monatsh. Chem. 1996, 127, 1063.
17. Recent leading reviews: (a) Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2209.
18. (b) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer; Berlin, 1999; Vol. 3, pp 1105.
19. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033.
20. (d) Alexakis, A.; Behhaim, C. Eur. J. Org. Chem. 2002, 3221.
21. (e) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
22. (a) Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.
23. (b) Haack, K.J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 285.
24. (c) Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
25. (a) Watanabe, M.; Murata, K.; Ikariya, T. J. Am. Chem. Soc. 2003. 125, 7508.
26. (b) Ikariya, T.; Wang, H.; Watanabe, M.; Murata, K. J. Organomet. Chem. 2004, 659, 1377.
27. (c) Murata, K.; Konishi, H.; Ito, M.; Ikariya, T. Organometallics 2002, 21, 253.
28. 3CN gave poor yields of the desired product, albeit with almost full conversion of the nitroalkenes because of polymerization of nitroalkenes promoted by the amido complex.
29. O- and C-bound metal enolato complexes: (a) Burkhardt, E. R.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 110, 2022.
30. (b) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938.
31. (c) Stack, J. G.; Doney, J. J.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 453.
32. (d) Hartwig, J. F.; Andersen. R. A.; Bergman, R. G. J. Am. Chem. Soc. 1990, 112, 5670.
33. (e) Culkin, D. A.; Hartwig, J. F. Acc. Chem Res. 2003, 36, 234 and references therein.
34. (f) Naota, T.; Tannna, A.; Kamuro, S.; Murahashi, S.-I. J. Am. Chem. Soc. 2002, 124, 6842.
35. (g) Majima, K.; Takita, R.; Okada, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 15837.
36. (a) Mulzer, J. J. Prakt. Chem. 1994, 336, 287.
37. (b) Mulzer, J.; Zuhse, R.; Schmiechen, R. Angew. Chem., Int. Ed. Engl. 1992, 31, 870.