Enhanced cooperativity through design: Pendant CoIII-salen polymer brush catalysts for the hydrolytic kinetic resolution of epichlorohydrin (salen=N,N'-bis(salicylidene)ethylenediamine dianion)

Chemistry - A European Journal

Volumn 14, Issue 24, 2008, Pages 7306-7313

  Gill, Christopher S ^a   Venkatasubbaiah, Krishnan ^a   Phan, Nam T S ^a   Weck, Marcus ^b,c   Jones, Christopher W ^a,b  

^a Georgia Institute of Technology   (United States)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^c NEW YORK UNIVERSITY   (United States)

Author keywords

Asymmetric synthesis; Cobalt salen; Heterogeneous catalysis; Kinetic resolution; Polymer brush

Indexed keywords

ASYMMETRIC SYNTHESIS; COBALT-SALEN; HETEROGENEOUS CATALYSIS; KINETIC RESOLUTION; POLYMER BRUSH;

COBALT; EPICHLOROHYDRIN; ETHYLENEDIAMINE DERIVATIVE; N,N' DISALICYLIDENEETHYLENEDIAMINE; POLYMER;

ARTICLE; CATALYSIS; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HYDROLYSIS; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TRANSMISSION ELECTRON MICROSCOPY;

CATALYSIS; COBALT; EPICHLOROHYDRIN; ETHYLENEDIAMINES; HYDROLYSIS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON, TRANSMISSION; POLYMERS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 53849141862     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800532     Document Type: Article

References (58)

1. a) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307-1315;
2. b) P. Kumar, V. Naidu, P. Gupta, Tetrahedron 2007, 63, 2745-2785.
3. L. P. C. Nielsen, C. P. Stevenson, D G. Blackmond, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 1360-1362.
4. a) J. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687-2688;
5. b) J. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432-1435;
6. Angew. Chem. Int. Ed. 2002, 41, 1374-1377;
7. c) R. I. Kureshy, S. Singh, N. U. H. Khan, S. H. R. Abdi, I. Ahmad, A. Bhatt, R. V. Jasra, Chirality 2005, 17, 590-594.
8. R. Breinbauer, E. N. Jacobsen, Angew. Chem. 2000, 112, 3750-3753;
9. Angew. Chem. Int. Ed. 2000, 39, 3604-3607.
10. a) D. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147-4154;
11. b) M. Holbach, M. Weck, J. Org. Chem. 2006, 71, 1825-1836;
12. c) B. M. Rossbach, K. Leopold, R. Weberskirch, Angew. Chem. 2006, 118, 1331-1335;
13. Angew. Chem. Int. Ed. 2006, 45, 1309-1312;
14. d) M. A. Kwon, G. J. Kim, Catal. Today 2003, 87, 145-151;
15. e) Y. M. Song, H. L. Chen, X. Q. Hu, C. M. Bai, Z. Zheng, Tetrahedron Lett. 2003, 44, 7081-7085;
16. f) Y. M. Song, X. O. Yao, H. L. Chen, C. M. Bai, X. Q. Hu, Z. Zheng, Tetrahedron Lett. 2002, 43, 6625-6627.
17. X. L. Zheng, C. W. Jones, M. Weck, Chem. Eur. J. 2006, 12, 576-583.
18. a) C. Li, Catal. Rev. Sci. Eng. 2004, 46, 419-492;
19. b) C. Baleizao, H. Garcia, Chem. Rev. 2006, 106, 3987-4043;
20. c) M. Heitbaum, F. Glorius, I. Escher, Angew. Chem. 2006, 118, 4850-4881;
21. Angew. Chem. Int. Ed. 2006, 45, 4732-4762.
22. a) H. Q. Yang, L. Zhang, L. Zhong, Q. H. Yang, C. Li, Angew. Chem. 2007, 119, 6985-6989;
23. Angew. Chem. Int. Ed. 2007, 46, 6861-6865;
24. b) H. Q. Yang, L. Zhang, W. G. Su, Q. H. Yang, C. Li, J. Catal. 2007, 248, 204-212.
25. a) G. J. Kim, D. W. Park, Catal. Today 2000, 63, 537-547;
26. b) S. S. Thakur, S. W. Chen, W. J. Li, C. K. Shin, S. J. Kim, Y. M. Koo, G. J. Kim, J. Organomet. Chem. 2006, 691, 1862-1872.
27. S. D. Choi, G. J. Kim, Catal. Lett. 2004, 92, 35-40.
28. C. R. Oh, D. J. Choo, W. H. Shim, D. H. Lee, E. J. Roh, S. Lee, C. E. Song, Chem. Commun. 2003, 1100-1101.
29. a) I. Shepperson, M. Cavazzini, G. Pozzi, S. Quici, J. Fluorine Chem. 2004, 125, 175-180;
30. b) M. Cavazzini, S. Quid, G. Pozzi, Tetrahedron 2002, 58, 3943-3949.
31. H. Mori, A. Boker, G. Krausch, A. H. E. Muller, Macromolecules 2001, 34, 6871-6882.
32. a) M. Mayr, B. Mayr, M. R. Buchmeiser, Angew. Chem. 2001, 113, 3957-3960;
33. Angew. Chem. Int. Ed. 2001, 40, 3839-3842;
34. b) M. R. Buchmeiser, S. Lubbad, M. Mayr, K. Wurst. Inorg. Chim. Acta 2003, 345, 145-153.
35. a) G. Sharma, M. Ballauff, Macromol. Rapid Commun. 2004, 25, 547-552;
36. b) Y. Mei, G. Sharma, Y. Lu, M. Ballauff, M. Drechsler, T. Irrgang, R. Kempe, Langmuir 2005, 21, 12229-12234;
37. c) G. Sharma, Y. Mei, Y. Lu, M. Ballauff, T. Irrgang, S. Proch, R. Kempe, J. Catal. 2007, 246, 10-14;
38. d) Y. Mei, Y. Lu, F. Polzer, M. Ballauff, M. Drechsler, Chem. Mater. 2007, 19, 1062-1069;
39. e) M. Schrinner, F. Polzer, Y. Mei, Y. Lu, B. Haupt, M. Ballauff, A. Goldel, M. Drechsler, J. Preussner, U. Glatzel, Macromol. Chem. Phys. 2007, 208, 1542-1547;
40. f) S. Proch, Y. Mei, J. M. R. Villanueva, Y. Lu, A. Karpov, M. Ballauff, R. Kempe, Adv. Synth. Catal. 2008, 350, 493-500.
41. X. Zheng, C. S. Gill, N. T. S. Phan, M. Weck, C. W. Jones in 20th North American Catalysis Society National Meeting, Houston, TX USA, 2007.
42. a) G. M. Sammis, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 4442-4443;
43. b) G. M. Sammis, H. Danjo, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 9928-9929;
44. c) E. K. Noh, S. J. Na, S. Sujith, S. W. Kim, B. Y. Lee, J. Am. Chem. Soc. 2007, 129, 8082-8083;
45. d) X. B. Lu, L. Shi, Y. M. Wang, R. Zhang, Y. J. Zhang, X. J. Peng, Z. C. Zhang, B. Li, J. Am. Chem. Soc. 2006, 128, 1664-1674;
46. e) F. X. Chen, B. Qin, X. M. Feng, G. L. Zhang, Y. Z. Jiang. Tetrahedron 2004, 60, 10449-10460;
47. f) S. S. Kim, J. M. Kwak, Tetrahedron 2006, 62, 49-53.
48. X. L. Zheng, C. W. Jones, M. Week, J. Am. Chem. Soc. 2007, 129, 1105-1112.
49. A. Marsh, A. Khan, M. Garcia, D. M. Haddleton, Chem. Commun. 2000, 2083-2084.
50. X. L. Zheng, C. W. Jones, M. Week, Adv. Synth. Catal. 2008, 350, 255-261.
51. J. H. Xia, K. Matyjaszewski, Macromolecules 1997, 30, 7692-7696.
52. Y. B. Sun, X. B. Ding, Z. H. Zheng, X. Cheng, X. H. Hu, Y. X. Peng, Eur. Polym. J. 2007, 43, 762-772.
53. C. Baleizao, B. Gigante, H. Garcia, A. Corma, J. Catal. 2003, 215, 199-207.
54. C. Baleizao, B. Gigante, M. J. Sabater, H. Garcia, A. Corma, Appl. Catal. A 2002, 228, 279-288.
55. S. Jain, X. L. Zheng, C. W. Jones, M. Week, R. J. Davis, Inorg. Chem. 2007, 46, 8887-8896.
56. A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518-1520.
57. J. C. Hicks, C. W. Jones, Langmuir 2006, 22, 2676-2681.
58. D. Y. Zhao, Q. S. Huo, J. L. Feng, B. F. Chmelka, G. D. Stucky, J. Am. Chem. Soc. 1998, 120, 6024-6036.