Enantioselective Michael Reaction of Malonates to Nitroolefins Catalyzed by Bifunctional Organocatalysts

Journal of the American Chemical Society

Volumn 125, Issue 42, 2003, Pages 12672-12673

  Okino, Tomotaka ^a   Hoashi, Yasutaka ^a   Takemoto, Yoshiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BASE; DIAMINE; KETENE DERIVATIVE; MALONIC ACID DERIVATIVE; NITRONE; PHENYL GROUP; PROLINE; THIOUREA DERIVATIVE;

ACIDITY; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BOND; MICHAEL ADDITION; PHASE TRANSITION; STOICHIOMETRY;

EID: 0142072631     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036972z     Document Type: Article

References (45)

1. For a review see: Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1877-1894.
2. (a) Johnson, T. A.; Jang, D. O.; Slafer, B. W.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2002, 124, 11689-11698.
3. (b) Schäfer, H.; Seebach, D. Tetrahedron 1995, 51, 2305-2324.
4. (c) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290.
5. (d) Kobayashi, N.; Iwai, K. J. Org. Chem. 1981, 46, 1823-1828.
6. Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193.
7. Hayashi, T. Synlett 2001, 879-887.
8. (a) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778.
9. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263.
10. (c) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80.
11. (a) 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, 13097-13105.
12. (b) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215-10216.
13. Brunner, H.; Kimel, B. Monatsh. Chem. 1996, 127, 1063-1072.
14. (a) Andrey, O.; Alexakis, A.; Bernardinelli, G. Org. Lett. 2003, 5, 2559-2561.
15. (b) Enders, D.; Seki, A. Synlett 2002, 26-28.
16. (c) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423-2425.
17. (d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260-5267.
18. For a review see: Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726-3748.
19. (a) Okino, T.; Hoashi, Y.; Takemoto, Y. Tetrahedron Lett. 2003, 44, 2817-2821.
20. (b) Curran, D. P.; Kuo, L. H. J. Org. Chem. 1994, 59, 3259-3261.
21. (c) Curran, D. P.; Kuo, L. H. Tetrahedron Lett. 1995, 37, 6647-6650.
22. (d) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217-220.
23. (e) Wittkopp, A.; Schreiner, P. R. Chem. Eur. J. 2003, 9, 407-414.
24. (f) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867-870.
25. (g) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012-10014.
26. (h) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964-12965.
27. (a) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842-1843.
28. (b) Cordova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866-1867.
29. (c) Northrup, A. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 6798-6799.
30. (a) Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1993, 34, 3453-3456.
31. (b) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200.
32. (c) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419-6420.
33. (a) Okino, T.; Takemoto, Y. Org. Lett. 2001, 3, 1515-1517.
34. (b) Dolling, U. H.; Davis, P.; Grabowski, E. J. J. J. Am. Chem. Soc. 1984, 106, 446-447.
35. (c) O'Donnell, M. J.; Bennett, W. D.; Wu, S. J. Am. Chem. Soc. 1989, 111, 2353-2355.
36. (d) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585.
37. (e) Ooi, T.; Takahashi, M.; Doda, K.; Maruoka, K. J. Am. Chem. Soc. 2002, 724, 7640-7641.
38. (f) Kita, T.; Georgieva, A.; Hashimoto, Y.; Nakata, T.; Nagasawa, K. Angew. Chem., Int. Ed. 2002, 41, 2832-2834.
39. (g) Ishikawa, T.; Araki, Y.; Kumamoto, T.; Seki, H.; Fukuda, K.; Isobe, T. Chem. Commun. 2001, 245-246.
40. (a) Etter, M. C.; Urbañczyk-Lipkowska, Z.; Zia-Ebrahimi, M.; Panunto, T. W. J. Am. Chem. Soc. 1990, 112, 8415-8426.
41. (b) Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072-7080.
42. (c) Linton, B. R.; Goodman, M. S.; Hamilton, A. D. Chem. Eur. J. 2000, 6, 2449-2455.
43. 8 solution of trans-β-nitrostylene or diethyl malonate with catalyst 1a resulted in no significant change of their resonances, since both of them might interact with 1a very weakly.
44. For a review of metallic bifunctional catalyst see: (a) Gröger, H. Chem. Eur. J. 2001, 7, 5246-5251.
45. (b) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256.