Control of four stereocenters in an organocatalytic domino double michael reaction: efficient synthesis of multisubstituted cyclopentanes

Organic Letters

Volumn 10, Issue 16, 2008, Pages 3425-3428

  Tan, Bin ^a   Shi, Zugui ^a   Chua, Pei Juan ^a   Zhong, Guofu ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

9 AMINO 9 DEOXYEPIQUININE; 9-AMINO-9-DEOXYEPIQUININE; CYCLOPENTANE DERIVATIVE; QUINOLIZINE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLOPENTANES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUINOLIZINES; STEREOISOMERISM;

EID: 54049111906     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801246m     Document Type: Article

References (56)

1. For a recent review, see: (a) Enders, D.; Grondai, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
2. (b) Chapman, C. J.; Frost, C. G. Synthesis 2007, 1.
3. For general reviews of organocatalysis, see: (a) Dalko, P. I., Ed. Enantioselective Organocatalysis: Reactions and Experimental Procedures; Wiley-VCH: Weinheim, 2007.
4. (b) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, 2005.
5. (c) Seayad, J.; List, B. Org. Biomol. Chem. 2005, 3, 719.
6. (d) Gaunt, M. J.; Johansson, C. C. C.; McNally, A.; Vo, N. T. Drug Discovery Today 2007, 2, 8.
7. (e) List, B. Chem. Commun. 2006, 819.
8. (a) Enders, D.; Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861.
9. (b) Enders, D.; Hüttl, M. R. M.; Runsink, J.; Raabe, G.; Wendt, B. Angew. Chem., Int. Ed. 2007, 46, 467.
10. (c) Mailand, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 1272.
11. (d) Marigo, M.; Bertelsen, S.; Landa, A.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 5475.
12. (e) Hayashi, Y.; Okano, T.; Aratake, S.; Hazelard, D. Angew. Chem., Int. Ed. 2007, 46, 4922.
13. (f) Cao, C.-L.; Sun, X.-L.; Kang, Y.-B.; Tang, Y. Org. Lett. 2007, 9, 4151.
14. For a review of tandem reactions, see: (a) Enders, D.; Grondal, C.; Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570.
15. For selected examples of tandem reactions, see: (b) Ramachary, D. B.; Chowdari, N. S.; Barbas III, C. F. Angew. Chem., Int. Ed. 2003, 42, 4233.
16. (c) Yamamoto, Y.; Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 5962.
17. (d) Zhong, G.; Yu, Y. Org. Lett. 2004, 6, 1637.
18. (e) Zhong, G. Chem. Commun. 2004, 626.
19. (f) Reyes, E.; Jiang, H.; Milelli, A.; Elsner, P.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 9202.
20. (g) Cabrera, S.; Alemán, J.; Bolze, P.; Bertelsen, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2008, 47, 121.
21. (h) Aroyan, C. E.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 256.
22. (i) Dudding, T.; Hafez, A. M.; Taggi, A. E.; Wagerle, T. R.; Lectka, T. Org. Lett. 2002, 4, 387.
23. (j) Wang, J.; Xie, H.; Li, H.; Zu, L.; Wang, W. Angew. Chem., Int. Ed. 2008, 47, 4177.
24. (k) Li, H.; Zhang, Y.; Vogel, P.; Sinay, P.; Bleriot, Y. Chem. Commun. 2007, 183.
25. (l) Marigo, M.; Schulte, T.; Franzen, J.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 15710.
26. (m) Casas, J.; Engqvist, M.; Ibrahem, L; Kaynak, B.; Córdova, A. Angew. Chem., Int. Ed. 2005, 44, 1343.
27. (n) Yang, J. W.; Hechavarria, M.; Fonseca, T.; List, B. J. Am. Chem. Soc. 2005, 127, 15036.
28. (o) Huang, Y.; Walji, A. M.; Larsen, C. H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 15051.
29. (p) Brandau, S.; Maerten, E.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 14986.
30. (q) Vicario, J. L.; Reboredo, S.; Badía, D.; Carrillo, L. Angew. Chem., Int. Ed. 2007, 46, 5168.
31. For selected reviews regarding Michel addition reactions, see: (a) Berner, O.; Tedeschi, M. L.; Enders, D. Eur. J. Org. Chem. 2002, 1877.
32. (b) Tsogoeva, S. B. Eur. J. Org. Chem. 2007, 1701.
33. (c) Almasi, D.; Alonso, D. A.; Nàjera, C. Tetrahedron: Asymmetry 2007, 18, 299.
34. (d) Vicario, J. L.; Badia, D.; Carrillo, L. Synthesis 2007, 2065.
35. Review of double Michael reactions, see: (a) Ihara, M.; Fukumoto, K. Angew. Chem., Int. Ed. 1993, 32, 1010.
36. Examples using chiral auxiliaries for asymmetric double Michael reactions, see: (a) Saito, S.; Hirohara, Y.; Narahara, O.; Moriwake, T. J. Am. Chem. Soc. 1989, 111, 4533.
37. (b) Dixon, D. J.; Ley, S. V.; Rodriguez, F. Angew. Chem., Int. Ed. 2006, 45, 4763.
38. Examples using chiral precursors for asymmetric double Michael reactions, see: (a) Paquette, L. A.; Tae, J.; Arrington, M. P.; Sadoun, A. H. J. Am. Chem. Soc. 2000, 122, 2742.
39. (b) Hagiwara, H.; Kobayashi, K.; Miya, S.; Hoshi, T.; Suzuki, T.; Ando, M. Org. Lett. 2001, 3, 251.
40. (c) Herzon, S. B.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 5342.
41. (d) Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128, 8678.
42. (a) Zu, L.; Xie, H.; Wang, J.; Tang, Y.; Wang, W. Angew. Chem., Int. Ed. 2007, 46, 3732.
43. (b) Li, H.; Zu, L.; Xie, H.; Wang, J.; Jiang, W.; Wang, W. Org. Lett. 2007, 9, 1833.
44. (c) Hoashi, Y.; Yabuta, T.; Takemoto, Y. Tetrahedron Lett. 2004, 45, 9185.
45. (d) Hoashi, Y.; Yabuta, T.; Yuan, P.; Miyabe, H.; Takemoto, Y. Tetrahedron 2006, 62, 365.
46. Tan, B.; Chua, P. J.; Li, Y.; Zhong, G. Org. Lett. 2008, 10, 2437.
47. For reviews of the synthesis and bioactivities of cyclopentanes, see: (a) Biaggio, F. C.; Rufino, A. R.; Zaim, M. H.; Zaim, C. Y. H.; Bueno, M. A.; Rodrigues, A. Curr. Org. Chem. 2005, 9, 419.
48. (b) Silva, L. F. Tetrahedron 2002, 58, 9137.
49. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
50. (d) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293.
51. Some papers related to using this type of catalyst: see (a) Xie, J.-W.; Chen, W.; Li, R.; Zeng, M.; Du, W.; Yue, L.; Chen, Y.-C.; Wu, Y.; Zhu, J.; Deng, J.-G. Angew. Chem., Int. Ed. 2007, 46, 389.
52. (b) Xie, J.-W.; Yue, L.; Chen, W.; Du, W.; Zhu, J.; Deng, J.-G.; Chen, Y.-C. Org. Lett. 2007, 9, 413.
53. (c) Bartoli, G.; Bosco, M.; Carlone, A.; Pesciaioli, F.; Sambri, L.; Melchiorre, P. Org. Lett. 2007, 9, 1403.
54. (d) McCooey, S. H.; Connon, S. J. Org. Lett. 2007, 9, 599.
55. (e) Zheng, B.-L.; Liu, Q.-Z.; Guo, C.-S.; Wang, X.-L.; He, L. Org. Biomol. Chem. 2007, 5, 2913.
56. Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chern. Soc. 2005, 127, 119.