Organocatalytic conjugate addition of nitroalkanes to 2H-chromene-3- carbaldehydes: Synthesis of highly functionalized chroman derivatives

Arkivoc

Volumn 2009, Issue 14, 2009, Pages 362-375

  Zhang, Jun Min ^a   Lou, Chun Liang ^a   Hu, Zhi Peng ^a   Yan, Ming ^a  

^a SUN YAT SEN UNIVERSITY   (China)

Author keywords

2H chromene 3 carbaldehyde; Chroman; Conjugate addition; Nitroalkane; Organocatalysis

Indexed keywords

EID: 77953195100     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0010.e30     Document Type: Article

References (37)

1. (a) Ellis, G. P. Chromenes, Chromanones, and Chromanones, and Chromones. In The Chemisry of Heterocyclic Compounds; Wiley: New York, 1977; Vol. 31, pp 11-139.
2. (b) Hepworth, J. In Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon; Oxford, UK, 1984; Vol. 3, pp 737-883.
3. (c) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G.-Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939.
4. (d) Nicolaou, K. C.; Pfefferkorn, J. A.; Mitchell, H. J.; Roecker, A. J.; Barluenga, S.; Cao, G. Q.; Affleck, R. L.; Lillig, J. E. J. Am. Chem. Soc. 2000, 122, 9954.
5. (e) Nicolaou, K. C.; Pfefferkorn, J. A.; Barluenga, S.; Mitchell, H. J.; Roecker, A. J.; Cao, G.-Q. J. Am. Chem. Soc. 2000, 122, 9968.
6. (f) Andrianasolo, E. H.; Haramaty, L.; Rosario-Passapera, R.; Bidle, K.; White, E.; Vetriani, C.; Falkowski, P.; Lutz, R. J. Nat. Prod. 2009, 72, 1216.
7. For the recent review of chroman derivatives with biological activity, see: Wang, G. X.; Wang, N. X.; Shi, T.; Yu, J. L.; Tang, X. L. Prog. Chem. 2008, 20, 518.
8. Kwak, J. H.; Kang, H. E.; Jung, J. K.; Kim, H.; Cho, J.; Lee, H. Arch. Pharm. Res. 2006, 29, 934.
9. Kanbe, Y.; Kim, M. H.; Nishimoto, M.; Ohtake, Y.; Kato, N.; Tsunenari, T.; Taniguchi, K.; Ohizumi, I.; Kaiho, S.; Morikawa, K.; Jo, J. C.; Lim, H. S.; Kim, H. Y. Bioorg. Med. Chem. 2006, 14, 4803.
10. Emami, S.; Kebriaeezadeh, A.; Zamani, M. J.; Shafiee, A. Bioorg. Med. Chem. Lett. 2006, 16, 1803.
11. Koufaki, M.; Kiziridi, C.; Alexi, X.; Alexis, M. N. Bioorg. Med. Chem. 2009, 17, 6432.
12. (a) Wang, Q. L.; She, X. G.; Ren, X. F.; Ma, J. Y.; Pan, X. F. Tetrahedron: Asymmetry 2004, 15, 29.
13. (b) Doi, F.; Ohara, T.; Ogamino, T.; Higashinakasu, K.; Hasegawa, K.; Nishiyama, S. B. Chem. Soc. Jpn. 2004, 77, 2257.
14. (c) Hashmi, A. S. K.; Rudolph, M.; Bats, J. W.; Frey, W.; Rominger, F.; Oeser, T. Chem. Eur. J. 2008, 14, 6672.
15. Lesch, B.; Bräse, S. Angew. Chem. Int. Ed. 2004, 43, 115.
16. (a) Loiodice, F.; Longo, A.; Bianco, P.; Tortorella, V. Tetrahedron: Asymmetry 1995, 6, 1001.
17. (b) Hatzenbuhler, N. T.; Baudy, R.; Evrard, D. A.; Failli, A.; Harrison, B. L.; Lenicek, S.; Mewshaw, R. E.; Saab, A.; Shah, U.; Sze, J.; Zhang, M.; Zhou, D.; Chlenov, M.; Kagan, M.; Golembieski, J.; Hornby, G.; Lai, M.; Smith, D. L.; Sullivan, K. M.; Schechter, L. E.; Andree, T. H. J. Med. Chem. 2008, 51, 6980.
18. (a) Nyerges, M.; Virányi, A.; Marth, G.; Dancsó, A.; Balaskó, G.; Toke, L. Synlett 2004, 2761.
19. (b) Virányi, A.; Marth, G.; Dancsó, A.; Balaskó, G.; Toke, L.; Nyerges, M. Tetrahedron 2006, 62, 8720.
20. For the reviews of activation of α, β-unsaturated aldehydes and ketones with secondary amines or primary amines, see:
21. (a) Erkkilä, A.; Majander, I.; Pihko, P. M. Chem. Rev. 2007, 107, 5416.
22. (b) Ouellet, S. G.; Walji, A. M.; Macmillan, D. W. C. Acc. Chem. Res. 2007, 40, 1327.
23. (c) Walji, A. M.; Macmillan, D. W. C. Synlett 2007, 1477.
24. (d) Mielgo, A.; Palomo, C. Chem. Asian J. 2008, 3, 922.
25. (e) Yu, X.; Wang, W. Org. Biomol. Chem. 2008, 6, 2037.
26. (f) Macmillan, D. W. C. Nature 2008, 455, 304.
27. (g) Enders, D.; Wang, C.; Liebich, J. X. Chem. Eur. J. 2009, 15, 11058.
28. (h) Xu, L. W.; Luo, J.; Lu, Y. Chem. Commun. 2009, 1807.
29. For the selected publications of organocatalytic conjugate addition of nitroalkanes to α, β-unsaturated aldehydes, see:
30. (a) Palomo, C.; Landa, A.; Mielgo, A.; Oiarbide, M.; Puente, A.; Vera, S. Angew. Chem. Int. Ed. 2007, 46, 8431.
31. (b) Zu, L.; Xie, H.; Li, Hao.; Wang, J.; Wang, W. Adv. Synth. Catal. 2007, 349, 2660.
32. (c) Gotoh, H.; Ishikawa, H.; Hayashi, Y. Org. Lett. 2007, 9, 5307.
33. (d) Hojabri, L.; Hartikka, A.; Moghaddam, F. M.; Arvidsson, P. I. Adv. Synth. Catal. 2007, 349, 740.
34. (e) Wang, Y.; Li, P.; Liang, X.; Zhang, T. Y.; Ye, J. Chem. Commun. 2008, 1232.
35. (a) Zhang, J. M.; Hu, Z. P.; Zhao, S. Q.; Yan, M. Tetrahedron 2009, 65, 802.
36. (b) Zhang, J. M.; Hu, Z. P.; Dong, L. T.; Xuan, Y. N.; Lou, C. L.; Yan, M. Tetrahedron: Asymmetry 2009, 20, 355.
37. (c) Vesely, J.; Zhao, G.-L.; Bartoszewicz, A.; Córdova, A. Tetrahedron Lett. 2008, 49, 4209.