Biomimetic catalysis with immobilised organometallic ruthenium complexes: Substrate- and regioselective transfer hydrogenation of ketones

Chemistry - A European Journal

Volumn 6, Issue 24, 2000, Pages 4604-4611

  Polborn, Kurt ^a   Severin, Key ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Catalysts; Hydrogenations; Molecular imprintmg; Ruthenium; Transition states

Indexed keywords

ETHYLENEDIAMINE DERIVATIVE; HYDROGEN; KETONE; KETONE DERIVATIVE; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CRYSTAL STRUCTURE; HYDROGENATION; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

CATALYSIS; HYDROGEN; KETONES; MOLECULAR MIMICRY; ORGANOMETALLIC COMPOUNDS; RUTHENIUM;

EID: 0034671282     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20001215)6:24<4604::AID-CHEM4604>3.0.CO;2-Y     Document Type: Article

References (50)

1. a) A. J. Kirby, Angew. Chem. 1996, 108, 770-790; Angew. Chem. Int. Ed. 1996, 35, 706-724;
2. a) A. J. Kirby, Angew. Chem. 1996, 108, 770-790; Angew. Chem. Int. Ed. 1996, 35, 706-724;
3. b) Y. Murakami, J. Kikuchi, Y. Hisaeda, O. Hayashida, Chem. Rev. 1996, 96, 721-758;
4. c) M. C. Feiters in Comprehensive Supramolecular Chemistry, Vol. 10 (Eds.: J.-M. Lehn, D. N. Reinhoudt, J. C. Atwood, J. E. Davies, D. D. Macnicol, F. Vögtle), pp. 267-360.
5. a) M. T. Reetz, S. R. Waldvogel, Angew. Chem. 1997, 109, 870-873; Angew. Chem. Int. Ed. Engl. 1997, 36, 865-867;
6. a) M. T. Reetz, S. R. Waldvogel, Angew. Chem. 1997, 109, 870-873; Angew. Chem. Int. Ed. Engl. 1997, 36, 865-867;
7. b) M. T. Reetz, C. Frömbgen, Synthesis, 1999, 9, 1555-1557;
8. c) R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997-2011.
9. a) J. M. Thomas, Angew. Chem. 1999, 111, 3800-3843; Angew. Chem. Int. Ed. 1999, 38, 3588-3628;
10. a) J. M. Thomas, Angew. Chem. 1999, 111, 3800-3843; Angew. Chem. Int. Ed. 1999, 38, 3588-3628;
11. b) E. J. Creyghton, R. S. Downing, J. Mol. Cat. A 1998, 134, 47-61.
12. a) B. Sellergren, Angew. Chem. 2000, 112, 1071-1078; Angew. Chem. Int. Ed. 2000, 39, 1031-1837;
13. a) B. Sellergren, Angew. Chem. 2000, 112, 1071-1078; Angew. Chem. Int. Ed. 2000, 39, 1031-1837;
14. b) K. Haupt, K. Mosbach, Trends Biotech. 1998, 16, 468-475;
15. c) G. Wulff, Angew. Chem. 1995, 107, 1958-1979; Angew. Chem. Int. Ed. Engl. 1995, 34, 1812-1832;
16. c) G. Wulff, Angew. Chem. 1995, 107, 1958-1979; Angew. Chem. Int. Ed. Engl. 1995, 34, 1812-1832;
17. d) M. E. Davies, A. Katz, W. R. Ahmad, Chem. Mater. 1996, 8, 1820-1839;
18. e) Molecular and Ionic Recognition with Imprinted Polymers (Eds.: R. A. Bartsch, M. Maeda), Oxford University Press, New York, 1998.
19. J. Matsui, I. A. Nicholls, I. Karube, K. Mosbach, J. Org. Chem. 1996, 61, 5414-5417.
20. a) P. Gamez, B. Dunjic, C. Pinel, M. Lemaire, Tetrahedron Lett. 1995, 36, 8779-8782;
21. b) F. Locatelli, P. Gamez, M. Lemaire, J. Mol. Catal. A 1998, 135, 89-98.
22. B. P. Santora, A. O. Larsen, M. R. Gagné, Organometallics 1998, 17, 3138-3140.
23. a) M. J. Palmer, M. Wills, Tetrahedron: Asymmetry 1999, 10, 2045-2061;
24. b) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102.
25. a) D. A. Alonso, P. Brandt, S. J. M. Nordin, P. G. Andersson, J. Am. Chem. Soc. 1999, 121, 9580-9588;
26. b) M. Yamakawa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466-1478.
27. K. Polborn, K. Severin, Chem. Commun. 1999, 2481-2482.
28. K. Polborn, K. Severin, Eur. J. Inorg. Chem. 2000, 1687-1692.
29. a) H. Brunner, Angew. Chem. 1999, 111, 1248-1263; Angew. Chem. Int. Ed. 1999, 38, 1194-1208;
30. a) H. Brunner, Angew. Chem. 1999, 111, 1248-1263; Angew. Chem. Int. Ed. 1999, 38, 1194-1208;
31. b) D. L. Davies, J. Fawcett, R. Krafczyk, D. R. Russell, J. Organomet. Chem. 1997, 545/546, 581-585.
32. a) G. Capper, L. C. Carter, D. L. Davies, J. Fawcett, D. R. Russell, J. Chem. Soc. Dalton Trans. 1996, 1399-1403;
33. b) L. Carter, D. L. Davies, J. Fawcett, D. R. Russell, Polyhedron 1993, 12, 1599-1602;
34. c) D. F. Dersnah, M. C. Baird, J. Organomet. Chem. 1977, 127, C55-C58.
35. a) K.-J. Haak, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297-300; Angew. Chem. Int. Ed. Engl. 1997, 36, 285-288;
36. a) K.-J. Haak, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297-300; Angew. Chem. Int. Ed. Engl. 1997, 36, 285-288;
37. b) S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562-7563.
38. a) J. Matsui, Y. Miyoshi, O. Doblhoff-Dier, T. Takeushi, Anal. Chem. 1995, 67, 4404-4408;
39. b) B. Sellergren, K. J. Shea, J. Chromatogr. 1993, 635, 31-49;
40. c) G. Vlatakis, L. I. Andersson, R. Müller, K. Mosbach, Nature 1993, 361, 645-647.
41. 31P).
42. K. Narita, M. Sekiya, Chem. Pharm. Bull. 1977, 25, 135-140.
43. According to ICP-AES measurements (Table 1) between 77 and 83 % of the ruthenium complexes have been incorporated.
44. Imprinted polymers have been used for the regioselective modification of steroids: a) C. Alexander, C. R. Smith, M. J. Whitcombe, E. N. Vulfson, J. Am. Chem. Soc. 1999, 121, 6640-6651;
45. b) S. E. Byström, A. Börje, B. Akermark, J. Am. Chem. Soc. 1993, 115, 2081-2083.
46. Strategies to generate catalytic systems with the help of transition state analogues have been discussed by Sanders: a) P. A. Brady, J. K. M. Sanders, Chem. Soc. Rev. 1997, 26, 327-336;
47. b) J. K. M. Sanders, Chem. Eur. J. 1998, 4, 1378-1383.
48. H. Kamogawa, A. Kanzawa, M. Kadoya, T. Naito, M. Nanasawa, Bull. Chem. Soc. Jpn. 1983, 56, 762-765.
49. J. Ren, K. Sakakibara, M. Hirota, Bull. Chem. Soc. Jpn. 1993, 66, 1897-1902.
50. M. A. Bennett, T-N. Huang, T. W. Matheson, A. K. Smith, Inorg. Synth. 1982, 21, 74-78.