Asymmetric synthesis of multifunctionalized pyrrolines by a ruthenium porphyrin-catalyzed three-component coupling reaction

Organic Letters

Volumn 7, Issue 24, 2005, Pages 5349-5352

  Xu, Hai Wei ^a   Li, Gong Yong ^a   Wong, Man Kin ^b   Che, Chi Ming ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28844498979     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050819n     Document Type: Article

References (59)

1. For reviews on asymmetric 1,3-dipolar cycloaddition reactions, see: (a) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Wiley: Huboken, NJ, 2003.
2. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
3. (c) Karlsson, S.; Högberg, H. E. Org. Prep. Proced. Int. 2001, 33, 105.
4. (d) Nájera, C.; Sansano, J. M. Curr. Org. Chem. 2003, 7, 1105.
5. For examples, see: (a) Dogan, Ö.; Öner, I.; Ülkii, D.; Arici, C.; Tetrahedron: Asymmetry 2002, 13, 2099.
6. (b) Karlsson, S.; Högberg, H.-E. J. Chem. Soc., Perkin Trans. 1 2002, 1076.
7. (c) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Nájera, C. Eur. J. Org. Chem. 2001, 3133.
8. (d) Garner, P.; Dogan, Ö.; Youngs, W. J.; Kennedy, V. O.; Protasiewicz, J.; Zaniewski, R. Tetrahedron 2001, 57, 71.
9. (e) Karlsson, S.; Högberg, H.-E. Tetrahedron: Asymmetry 2001, 12, 1975.
10. (f) Karlsson, S.; Högberg, H.-E. Tetrahedron: Asymmetry 2001, 12, 1977.
11. (g) Enders, D.; Meyer, I.; Runsink, J.; Raabe, G. Tetrahedron 1998, 54, 10733.
12. (h) Grigg, R. Tetrahedron: Asymmetry 1995, 6, 2475.
13. (i) Garner, P.; Dogan, O. J. Org. Chem. 1994, 59, 4.
14. (j) Deprez, P.; Royer, J.; Husson, H.-P. Tetrahedron: Asymmetry 1991, 2, 1189.
15. For examples, see: (a) Ruano, J. L. G.; Tito, A.; Peromingo, M. T. J. Org. Chem. 2003, 68, 10013.
16. (b) Kagoshima, H.; Okamura, T.; Akiyama, T. J. Am. Chem. Soc. 2001, 123, 7182.
17. (c) Barluenga, J.; Fernández-Rodríguez, M. A.; Aguilar, E.; Fernández-Marí, F.; Salinas, A.; Olano, B. Chem. Eur. J. 2001, 7, 3533.
18. (d) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamamoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473.
19. (e) Coulter, T.; Grigg, R.; Malone, J. F.; Sridharan, V. Tetrahedron Lett. 1991, 32, 5417.
20. (f) Barr, D. A.; Dorrity, M. J.; Grigg, R.; Malone, J. F.; Montgomery, J.; Rajviroongit, S.; Stevenson, P. Tetrahedron Lett. 1990, 31, 6569.
21. (g) Kanemasa, S.; Yamamoto, H.; Tetrahedron Lett. 1990, 31, 3633.
22. For examples, see: (a) Chen, C.; Li, X.; Schreiber, S. L. J. Am. Chem. Soc. 2003, 125, 10174.
23. (b) Oderaotoshi, Y.; Cheng, W.; Fujitomi, S.; Kasano, Y.; Minakata, S.; Komatsu, M. Org. Lett. 2003, 5, 5043.
24. (c) Longmire, J. M.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 13400.
25. (d) Gothelf, A. S.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 4236.
26. (e) Allway, P.; Grigg, R. Tetrahedron Lett. 1991, 32, 5817.
27. (a) Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Klaus, S.; Strübing, D.; Beller, M. Chem. Eur. J. 2003, 9, 4286.
28. (b) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
29. (c) An, H.; Dan Cook, P. Chem. Rev. 2000, 100, 3311.
30. (d) Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. A. Acc. Chem. Res. 1996, 29, 123.
31. Works by us: (a) Zhou, C.-Y.; Yu, W.-Y.; Chan, P. W. H.; Che, C.-M. J. Org. Chem. 2004, 69, 7072.
32. (b) Zhang, J.-L.; Chan, P. W. H.; Che, C.-M. Tetrahedron Lett. 2003, 44, 8733.
33. (c) Zhou, C.-Y.; Chan, P. W. H.; Yu, W.-Y.; Che, C.-M. Synthesis 2003, 9, 1402.
34. (d) Cheung, W.-H.; Zheng, S.-L.; Yu, W.-Y.; Zhou, G.-C.; Che, C.-M. Org. Lett. 2003, 5, 2535.
35. (e) Zhou, C.-Y.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2002, 4, 3235.
36. (f) Zhang, J.-L.; Che, C.-M. Org. Lett. 2002, 4, 1911.
37. (g) Zheng, S.-L.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2002, 4, 889.
38. (h) Li, Y.; Huang, J.-S.; Zhou, Z.-Y.; Che, C.-M. J. Am. Chem. Soc. 2001, 123, 4843.
39. (i) Che, C.-M.; Huang J.-S.; Lee, F.-W.; Li, Y.; Lai, T.-S.; Kwong, H.-L.; Teng, P.-F.; Lee, W.-S.; Lo, W.-C.; Peng, S.-M.; Zhou, Z.-Y. J. Am. Chem. Soc. 2001, 123, 4119.
40. (j) Lo, W.-C.; Che, C.-M.; Cheng, K.-F.; Mak, T. C.-W. J. Chem. Soc., Chem. Commun. 1997, 1205.
41. Works by others: (a) Mirafzal, G. A.; Cheng, G.; Woo, L. K. J. Am. Chem. Soc. 2002, 124, 176.
42. (b) Hamaker, C. G.; Djukic, J.-P. Smith, D. A.; Woo, L. K. Organometallics 2001, 20, 5189.
43. (c) Simonneaux, G.; Galardon, E.; Paul-Roth, C.; Gulea, M.; Masson, S. J. Organomet. Chem. 2001, 617-618, 360.
44. (d) Galardon, E.; Maux, P. L.; Simonneaux, G. Tetrahedron 2000, 56, 615.
45. (e) Gross, Z.; Galili, N.; Simkhovich, L. Tetrahedron Lett. 1999, 40, 1571.
46. (f) Galardon, E.; Roué, S.; Maux, P. L.; Simonneaux, G. Tetrahedron Lett. 1998, 39, 2333.
47. (g) Galardon, E.; Maux, P. L.; Simonneaux, G. J. Chem. Soc., Perkin Trans. 1 1997, 2455.
48. (h) Galardon, E.; Maux, P. L.; Simonneaux, G. Chem. Commun. 1997, 927.
49. (i) Frauenkron, M.; Berkessel, A. Tetrahedron Lett. 1997, 38, 7175.
50. (j) Smith, D. A.; Reynolds, D. N.; Woo, L. K. J. Am. Chem. Soc. 1993, 115, 2511.
51. (a) Li, Y.; Chan, P. W. H.; Zhu, N.-Y.; Che, C.-M.; Kwong, H.-L. Organometallics 2004, 23, 54.
52. (b) Li, G.-Y.; Chen, J.; Yu, W.-Y.; Hong, W.; Che, C.-M. Org. Lett. 2003, 5, 2153.
53. For a copper-catalyzed three-component coupling reaction for pyrrolidine synthesis, see: Galliford, C. V.; Beenen, M. A.; Nguyen, S. T.; Scheidt, K. A. Org. Lett. 2003, 5, 3487.
54. For examples on three-component 1,3-dipolar cycloaddition reactions, see: (a) Fokas, D.; Ryan, W. J.; Casebier, D. S.; Coffen, D. L. Tetrahedron Lett. 1998, 39, 2235.
55. (b) Hamper, B. C.; Dukesherer, D. R.; South, M. S. Tetrahedron Lett. 1996, 37, 3671.
56. (c) Murphy, M. M.; Schullek, J. R.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1995, 117, 7029.
57. (a) Reference 6i.
58. (b) Li, Y.; Huang, J.-S.; Xu, G.-B.; Zhu, N.; Zhou, Z.-Y.; Che, C.-M.; Wong, K.-Y. Chem. Eur. J. 2004, 10, 3486.
59. Several attempts failed to obtain crystalline solids of the cycloaddition products for absolute configuration determination by X-ray crystallography analysis. Current efforts are directed toward the preparation of other pyrroline analogues for X-ray crystallography analysis.