Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts

Organic Letters

Volumn 7, Issue 10, 2005, Pages 1967-1969

  Vakulya, Benedek ^a   Varga, Szilárd ^a   Csámpai, Antal ^b   Soós, Tibor ^a  

^a CHEMICAL RESEARCH CENTER   (Hungary)

^b EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CHALCONE DERIVATIVE; CINCHONA ALKALOID; NITROMETHANE; ORGANIC COMPOUND; THIOUREA;

ARTICLE; CATALYST; CHIRALITY; CONJUGATE; ENANTIOSELECTIVITY; MICHAEL ADDITION; QUANTUM YIELD; SYNTHESIS;

CATALYSIS; CHALCONES; CINCHONA; CINCHONA ALKALOIDS; METHANE; MOLECULAR STRUCTURE; NITROPARAFFINS; STEREOISOMERISM; THIOUREA;

EID: 19544393388     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050431s     Document Type: Article

References (44)

1. Recent reviews dealing with enantioselective conjugate addition: (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5138.
2. (b) Berner, O. E.; Tedeschi, L.; Enders, D. Eur. J. Org. Chem. 2002, 1788.
3. (c) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
4. (d) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
5. Recent review with extensive literature background: Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933.
6. Methods using chiral metal complexes: (a) Yamaguchi M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 35, 8233.
7. (b) Yamaguchi M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223.
8. (c) Keller, E.; Veldman, N.; Spek, A. L.; Feringa, B. L. Tetrahedron: Asymmetry 1997, 8, 3403.
9. (d) Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557.
10. Methods using phase transfer catalysts: (a) Collona, S.; Hiemstra, H.; Wynberg, H. J. Chem. Soc., Chem. Commun. 1978, 238.
11. (b) Bakó, P.; Szöllo″sy, A.; Bombicz, P.; T″oke. L. Synlett 1997, 291.
12. (c) Corey, E. J.; Zhang, F.-Y. Org. Lett. 2000, 2, 4257.
13. (d) Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933.
14. (e) Sundararajan, G.; Prabagaran, N. Org. Lett. 2001, 3, 389.
15. Methods using secondary amine- or guanidine-based organocatalysts: (a) Davis, A. P.; Dempsey, K. J. Tetrahedron: Asymmetry 1995, 6, 2829.
16. (b) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975.
17. (c) Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331.
18. (d) Allingham, M. T.; Howard-Jones, A.; Murphy, P. J.; Thomas, D. A.; Caulkett, P. W. R. Tetrahedron Lett. 2003, 44, 8677
19. Recent reviews on cinchona alkaloids: (a) Tian, S.-K.; Chen, Y.; Hang, J.; Tang, L.; Deng, L. Acc. Chem. Res. 2004, 37, 621.
20. (b) Kacprzak, K.; Gawronski, J. Synthesis 2001, 961.
21. Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 417.
22. Sera, A.; Takagi, K.; Katayama, H.; Yamada, H. J. Org. Chem. 1988, 53, 1157.
23. Other bifunctional cinchona alkaloid-based catalytic applications: (a) France, S.; Shah, M. H.; Wheatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206.
24. (b) Liu, X.; Li, H.; Deng, L. Org. Lett. 2005, 7, 167.
25. (c) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2004, 43, 2.
26. (d) Li, H.; Wang, Y.; Tang, L.; Wu, F.; Liu, X.; Guo, C.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2004, 43, 105.
27. (e) Li, H.; Wang, Y.; Tang, L.; Deng L. J. Am. Chem. Soc. 2004, 126, 9906.
28. (f) Saaby, S.; Bella, M.; Jørgensen, K. A. J. Am. Chem. Soc. 2004, 126, 8120.
29. (g) Kawahara, S.; Nakano, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2003, 5, 3103.
30. (h) Balan, D.; Adolfsson, H. Tetrahedron Lett. 2003, 44, 2521.
31. (i) Shi, M.; Xu, Y.-M. Angew. Chem., Int. Ed. 2002, 41, 4507.
32. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
33. Most recent papers using thiourea catalysts: (a) Berkessel, A.; Cleemann, F.; Mukherjee, S.; Müller, T. N.; Lex, J. Angew. Chem., Int. Ed. 2005, 44, 807.
34. (b) Yoon, T. P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 466.
35. (c) Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.
36. (d) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558.
37. (e) Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
38. (f) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 119.
39. (g) Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625.
40. (h) Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2004, 45, 5589.
41. (i). Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
42. (j) Schreiner, P. R.; Wittkopp, A. Org. Lett. 2002, 4, 217.
43. For details see Supporting Information.
44. Botteghi, C.; Paganelli, S.; Schionato, A.; Boga, C.; Fava, A. J. Mol. Catal. 1991, 66, 7.