Recyclable polymer- and silica-supported Ruthenium(II)-Salen bis-pyridine catalysts for the asymmetric cyclopropanation of olefins

Advanced Synthesis and Catalysis

Volumn 351, Issue 9, 2009, Pages 1344-1354

  Gill, Christopher S ^a   Venkatasubbaiah, Krishnan ^a   Jones, Christopher W ^a,b  

^a Georgia Institute of Technology   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Asymmetric cyclopropanation; Enantioselectivity; Heterogeneous catalysis; Ruthenium salen; Supported catalysts

Indexed keywords

EID: 67549119254     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800779     Document Type: Article

References (50)

1. a) W. A. Donaldson, Tetrahedron 2001, 57, 8589;
2. b) J.Salaun, Chem. Rev. 1989, 89, 1247;
3. c) O. Lopez, J. G.Fernandez-Bolanos, M. V. Gil, Green Chem. 2005, 7, 431.
4. a) M. P. Doyle, D. C. Forbes, Chem. Rev. 1998, 98, 911;
5. b) M. P. Doyle, M. N Protopopova, Tetrahedron 1998, 54, 7919;
6. c) H. Lebel, J. F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977;
7. d) H. Pellissier, Tetrahedron 2008, 64, 7041;
8. e) G. Maas, Chem. Soc. Rev. 2004, 33, 183;
9. f) T Katsuki, Adv. Synth. Catal. 2002, 344,131;
10. g) T. Katsuki, Synlett 2003, 281.
11. J. A. Miller, W. C. Jin, S. T Nguyen, Angew. Chem. 2002, 114, 3077;
12. Angew. Chem. Int. Ed. 2002, 41, 2953.
13. a) J. A. Miller, E. J. Hennessy, W. J. Marshall, M. A. Scialdone, S. T. Nguyen, J. Org. Chem. 2003, 68, 7884;
14. b) J. A. Miller, B. A. Gross, M. A. Zhuravel, W. C. Jin, S. T. Nguyen, Angew. Chem. 2005, 117, 3953;
15. Angew. Chem. Int. Ed. 2005, 44, 3885.
16. a) C. E. Song, S. G. Lee, Chem. Rev. 2002, 102, 3495;
17. b) S. Bräse, F. Lauterwasser, R. E. Ziegert, Adv. Synth. Catal. 2003, 345, 869.
18. J. M. Fraile, J. I. Garcia, J. A. Mayoral, Coord. Chem. Rev. 2008, 252, 624.
19. A. Cornejo, J. M. Fraile, J. I. Garcia, M.J. Gil, S.V. Luis, V. Martinez-Merino, J. A. Mayoral, J. Org. Chem. 2005, 70, 5536.
20. A. Cornejo, J. M. Fraile, J. I. Garcia, E. Garcia-Verdugo, M. J. Gil, G Legarreta, S. V. Luis, V. MartinezMerino, J. A. Mayoral, Org. Lett. 2002, 4, 3927.
21. A. Cornejo, J. M. Fraile, J. I. Garcia, M. J. Gil, V. Martinez-Merino, J. A. Mayoral, Tetrahedron 2005, 61, 12107.
22. A. Cornejo, J. M. Fraile, J. I. Garcia, M.J. Gil, S. V. Luis, V. Martinez-Merino, J. A. Mayoral, C. R. Chim. 2004, 7, 161.
23. Y. Ferrand, P. Le Maux, G. Simonneaux, Tetrahedron: Asymmetry 2005, 16, 3829.
24. J. L. Zhang, Y. L. Liu, C. M. Che, Chem. Commun. 2002, 2906.
25. S. Syukri, W. Sun, F. E. Kühn, Tetrahedron Lett. 2007, 48, 1613.
26. C. S. Gill, K. Venkatasubbaiah, N. T. S. Phan, M. Week, C. W. Jones, Chem. Eur. J. 2008, 14, 7306.
27. a) M. Holbach, M. Weck, J. Org. Chem. 2006, 71, 1825;
28. b) X. L. Zheng, C. W. Jones, M. Week, Chem. Eur. J. 2006, 12, 576.
29. X. L. Zheng, C. W. Jones, M. Week, J. Am. Chem. Soc. 2007, 129, 1105.
30. X. L. Zheng, C. W. Jones, M. Week, Adv. Synth. Catal. 2008, 350, 255.
31. S. Jain, X. L. Zheng, C. W. Jones, M. Week, R. J. Davis, Inorg. Chem. 2007, 46, 8887.
32. M. Holbach, X. L. Zheng, C. Burd, C. W. Jones, M. Week, J. Org. Chem. 2006, 71, 2903.
33. A. Heckel, D. Seebach, Helv. Chim. Acta 2002, 85, 913.
34. N. Madhavan, C. W. Jones, M. Week, Acc. Chem. Res. 2008, 41, 1153.
35. S. Kannan, R. Ramesh, Polyhedron 2006, 25, 3095.
36. K. N. Kumar, G. Venkatachalam, R. Ramesh, Y. Liu, Polyhedron 2008, 27,157.
37. M. S. Refat, S. A. Ei-Korashy, D. N. Kumar, A. S. Ahmed, Spectrochim. Acta Part A 2008, 70, 898.
38. C. Baleizao, B. Gigante, H. Garcia, A. Corma, J. Catal. 2003, 215, 199.
39. The slight difference in selectivities between 4a and 4b may possibly be explained by the shorter linker of 4a compared to 4b. Due to the closer proximity of the polymer backbone to the Ru-salen active site for 4a, increased steric interference may be causing the slight drop in selectivity. The longer, flexible linker of 4b may lessen the steric hindrance, thereby producing higher selectivities.
40. J. L. Liang, X. Q. Yu, C. M. Che, Chem. Commun. 2002, 124.
41. L. Mishra, R. Prajapati, K. K. Pandey, Spectrochim. Acta Part A 2008, 70, 79.
42. S. S. Lee, S. Hadinoto, J. Y. Ying, Adv. Synth. Catal. 2006, 348, 1248;
43. a) S. S. Lee, J. Y. Ying, J. Mol. Catal. A: Chem. 2006, 256, 219.
44. a) J. M. Fraile, J. I. Garcia, C. I. Herrerias, J. A. Mayoral, S. Gmough, M. Vaultier, Green Chem. 2004, 6, 93;
45. b) J. H. Lim, S. N Riduan, S. S. Lee, J. Y. Ying, Adv. Synth. Catal. 2008, 350,1295;
46. c) A. Mandoli, S. Orlandi, D. Pini, P. Salvadori, Chem. Commun. 2003, 2466;
47. d) H. Werner, C. I. Herrerias, M. Glos, A. Gissibl, J. M. Fraile, I. Perez, J. A. Mayoral, O. Reiser, Adv. Synth. Catal. 2006, 348, 125.
48. A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518.
49. a) D. Y. Zhao, Q. S. Huo, J. L. Feng, B. F. Chmelka, G. D. Stucky, J. Am. Chem. Soc. 1998, 120, 6024;
50. b) J. C. Hicks, C. W. Jones, Langmuir 2006, 22, 2676.