Proline-induced enantioselective heterogeneous catalytic hydrogenation of isophorone on basic polymer-supported Pd catalysts

Catalysis Science and Technology

Volumn 5, Issue 2, 2015, Pages 716-723

  Schäfer, Christian ^a   Mhadgut, Shilpa C ^a,b   Kugyela, Nándor ^a   Török, Marianna ^a,b   Török, Béla ^a,b  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

^b MICHIGAN TECHNOLOGICAL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CATALYSTS; ENANTIOSELECTIVITY; HYDROGENATION; POLYMERS; SURFACE REACTIONS;

AMIDO GROUPS; ASYMMETRIC HYDROGENATION; CATALYTIC HYDROGENATION; ENANTIOSELECTION; ENANTIOSELECTIVE; FTIR SPECTROSCOPY; HYDROGEN PRESSURES; POLYMER-SUPPORTED;

CATALYST SUPPORTS;

EID: 84927802467     PISSN: 20444753     EISSN: 20444761     Source Type: Journal    
DOI: 10.1039/c4cy00954a     Document Type: Article

References (52)

1. G. Kyriakou, S. K. Beumont and R. M. Lambert, Langmuir, 2011, 27, 9687;
2. A. Kulkarni and B. Török, Curr. Org. Synth., 2011, 8, 187;
3. M. Bartók, Curr. Org. Chem., 2006, 10, 1533;
4. M. Studer, H.-U. Blaser and C. Exner, Adv. Synth. Catal., 2003, 345, 45;
5. T. Bürgi and A. Baiker, Acc. Chem. Res., 2004, 37, 909;
6. A. Baiker, Catal. Today, 2005, 100, 159.
7. F. Meemken, K. Hungerbühler and A. Baiker, Angew. Chem., Int. Ed., 2014, 53, 8640;
8. J. L. Margitfalvi and E. Tálas, Catal. Commun., 2014, 46, 142;
9. G. Martin, P. Mäki-Arvela, D. Y. Murzin and T. Salmi, Catal. Sci. Technol., 2014, 4, 170, early view.
10. Z. Makra and G. Szöllösi, Catal. Commun., 2014, 46, 113;
11. H. Ogawa, T. Mameda, T. Misaki, Y. Okamoto and T. Sugimura, Chem. Lett., 2013, 42, 813;
12. E. Schmidt, C. Bucher, G. Santarossa, T. Mallat, R. Gilmour and A. Baiker, J. Catal., 2012, 289, 238;
13. S. Tan, J. R. Monnier and C. T. Williams, Top. Catal., 2012, 55, 512.
14. T. Osawa, T. Kizawa, F. Takano, S. Ikeda, T. Kitamura, Y. Inoue and V. Borovkov, ChemCatChem, 2014, 6, 170;
15. T. Osawa and V. Borovkov, Recent Patents on Catalysis, 2012, 1, 27;
16. T. Osawa, I.-Y. Sandy Lee, S. Ikeda, T. Kitamura, Y. Inoue and V. Borovkov, Appl. Catal., A, 2012, 445/446, 259.
17. A. Tungler, T. Máthé, J. Petró and T. Tarnai, J. Mol. Catal., 1990, 61, 259.
18. E. Szabados, N. Györffy, A. Tungler, J. Balla and L. Konczol, React. Kinet., Mech. Catal., 2014, 111, 107;
19. N. Györffy and A. Tungler, J. Mol. Catal. A: Chem., 2011, 336, 72;
20. N. Györffy, A. Tungler and M. Fodor, J. Catal., 2010, 270, 2;
21. M. Fodor, A. Tungler and L. Vida, Catal. Today, 2009, 140, 58.
22. S. K. Beaumont, G. Kyriakou, D. J. Watson, O. P. H. Vaughan, A. C. Papageorgiou and R. M. Lambert, J. Phys. Chem. C, 2010, 114, 15075;
23. E. Zhan, S. Li, Y. Xu and W. Shena, Catal. Commun., 2007, 8, 1239;
24. S. Li, E. Zhan, Y. Li, Y. Xu and W. Shen, Catal. Today, 2008, 131, 347;
25. A. I. McIntosh, D. J. Watson and R. M. Lambert, Langmuir, 2007, 23, 6113;
26. A. I. McIntosh, D. J. Watson, J. W. Burton and R. M. Lambert, J. Am. Chem. Soc., 2006, 128, 7329.
27. S. C. Mhadgut, M. Török, J. Esquibel and B. Török, J. Catal., 2006, 238, 441.
28. S. C. Mhadgut, M. Török, S. Dasgupta and B. Török, Catal. Lett., 2008, 123, 156.
29. É. Sipos, A. Tungler and I. Bitter, New chiral modifier for enantioselective heterogeneous catalytic hydrogenation, in Catalysis in Organic Reactions, ed. D. J. Morell, Marcel Dekker, New York, 2002, p. 653;
30. É. Sipos, A. Tungler, I. Bitter and M. Kubinyi, J. Mol. Catal. A: Chem., 2002, 186, 187;
31. É. Sipos, A. Tungler and I. Bitter, J. Mol. Catal. A: Chem., 2003, 198, 167.
32. B. Török, A. Kulkarni, R. DeSousa, K. Satuluri, M. Török and G. K. S. Prakash, Catal. Lett., 2011, 141, 1435.
33. S. Bhaduri, V. S. Darshane, K. Sharma and D. Mukesh, J. Chem. Soc., Chem. Commun., 1992, 1738.
34. X. B. Zuo, H. F. Liu and M. H. Liu, Tetrahedron Lett., 1998, 39, 1941;
35. X. B. Zuo, H. F. Liu, D. W. Guo and X. Z. Yang, Tetrahedron, 1999, 55, 7787.
36. A. Bykov, V. Matveeva, M. Sulman, P. Valetskiy, O. Tkachenko, L. Kustov, L. Bronstein and E. Sulman, Catal. Today, 2009, 140, 64;
37. L. Yu, Z. Wang, J. Wu, S. Tu and K. Ding, Angew. Chem., Int. Ed., 2010, 49, 3627.
38. M. Benkhaled, S. Morin, C. Pichon, C. Thomazeau, C. Verdon and D. Uzio, Appl. Catal., A, 2006, 312, 1;
39. Y. Uozumi, Top. Curr. Chem., 2004, 242, 77;
40. M. C. Greca, C. Moraes and A. M. Segadaes, Appl. Catal., A, 2001, 216, 267.
41. X. Yu and W. Wang, Org. Biomol. Chem., 2008, 6, 2037;
42. M. Gruttadauria, F. Giacalone and R. Noto, Chem. Soc. Rev., 2008, 37, 1666;
43. W. Notz, F. Tanaka and C. F. Barbas, Acc. Chem. Res., 2004, 37, 580;
44. S. Bahmanyar, K. N. Houk, H. J. Martin and B. List, J. Am. Chem. Soc., 2003, 125, 2475;
45. B. List, Tetrahedron, 2002, 58, 5573.
46. D. J. Watson, R. B. R. John Jesudason, S. K. Beaumont, G. Kyriakou, J. W. Burton and R. M. Lambert, J. Am. Chem. Soc., 2009, 131, 14584.
47. B. Török, K. Felföldi, G. Szakonyi, K. Balázsik and M. Bartók, Catal. Lett., 1998, 52, 81;
48. M. Bartók, K. Felföldi, B. Török and T. Bartók, Chem. Commun., 1998, 2605;
49. B. Török, K. Felföldi, K. Balázsik and M. Bartók, Chem. Commun., 1999, 1725;
50. B. Török, M. Abid, G. London, J. Esquibel, M. Török, S. C. Mhadgut, P. Yan and G. K. S. Prakash, Angew. Chem., Int. Ed., 2005, 44, 3086.
51. The potential role of the diastereomeric DHIP-Pro adduct as a chiral modifier in the reaction has been raised by one of the reviewers.
52. S. Li, C. Chen, E. Zhan, S.-B. Liub and W. Shen, J. Mol. Catal. A: Chem., 2009, 304, 88.