Enantioselective access to chiral drugs by using asymmetric hydrogenation catalyzed by Rh(P-OP) complexes

Chemistry - A European Journal

Volumn 17, Issue 50, 2011, Pages 13978-13982

  Etayo, Pablo ^a   Núñez Rico, José Luis ^a   Fernández Pérez, Héctor ^a   Vidal Ferran, Anton ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

Author keywords

asymmetric catalysis; enantioselectivity; functionalized alkenes; hydrogenation; rhodium

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC HYDROGENATION; BUILDING BLOCKES; CHIRAL DRUGS; ENANTIOSELECTIVE; ENANTIOSELECTIVE CATALYSTS; FUNCTIONALIZED; NORBORNADIENE; RHODIUM COMPLEXES; RIVASTIGMINE;

CATALYSIS; ENANTIOMERS; ENANTIOSELECTIVITY; HYDROGENATION; OLEFINS; RHODIUM;

RHODIUM COMPOUNDS;

ALKENE; DRUG; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGENATION; STEREOISOMERISM;

ALKENES; CATALYSIS; HYDROGENATION; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; RHODIUM; STEREOISOMERISM;

EID: 82955222219     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103014     Document Type: Article

References (54)

1. V. Farina, J. T. Reeves, C. H. Senanayake, J. J. Song, Chem. Rev. 2006, 106, 2734
2. Asymmetric Catalysis on Industrial Scale: Challenges, Approaches, and Solutions, 2 nd ed., (Eds.: H.-U. Blaser, H.-J. Federsel,), Wiley-VCH, Weinheim, 2010.
3. S. J. Roseblade, A. Pfaltz, Acc. Chem. Res. 2007, 40, 1402
4. Phosphorus Ligands in Asymmetric Catalysis Vol. I-III, 1 st ed., (Ed.: A. Börner,), Wiley-VCH, Weinheim, 2008
5. J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713.
6. T. C. Nugent, M. El-Shazly, Adv. Synth. Catal. 2010, 352, 753
7. C. A. Busacca, D. R. Fandrick, J. J. Song, C. H. Senanayake, Adv. Synth. Catal. 2011, 353, 1825.
8. For a comprehensive review describing the synthesis of this kind of phosphorus ligands and their applications in asymmetric catalysis, see:, H. Fernández-Pérez, P. Etayo, A. Panossian, A. Vidal-Ferran, Chem. Rev. 2011, 111, 2119.
9. A. Panossian, H. Fernández-Pérez, D. Popa, A. Vidal-Ferran, Tetrahedron: Asymmetry 2010, 21, 2281.
10. J. L. Núñez-Rico, H. Fernández-Pérez, J. Benet-Buchholz, A. Vidal-Ferran, Organometallics 2010, 29, 6627.
11. H. Fernández-Pérez, M. A. Pericàs, A. Vidal-Ferran, Adv. Synth. Catal. 2008, 350, 1984
12. S. M. A. Donald, A. Vidal-Ferran, F. Maseras, Can. J. Chem. 2009, 87, 1273
13. H. Fernández-Pérez, S. M. A. Donald, I. J. Munslow, J. Benet-Buchholz, F. Maseras, A. Vidal-Ferran, Chem. Eur. J. 2010, 16, 6495
14. H. Fernández-Pérez, P. Etayo, J. L. Núñez- Rico, A. Vidal-Ferran, Chim. Oggi 2010, 28, XXVI.
15. For a closely related precedent on such a side reaction, see, S. E. Ramer, R. N. Moore, J. C. Vederas, Can. J. Chem. 1986, 64, 706.
16. S.-H. Park, S.-H. Kang, S.-H. Lim, H.-S. Oh, K.-H. Lee, Bioorg. Med. Chem. Lett. 2003, 13, 3455
17. S.-H. Park, H.-S. Oh, M.-A. Kang, H. Cho, J. B. Prasad, J. Won, K.-H. Lee, Bioorg. Med. Chem. 2007, 15, 3938, and references therein.
18. See, W. S. Knowles, Angew. Chem. 2002, 114, 2096
19. Angew. Chem. Int. Ed. 2002, 41, 1998, and references therein.
20. H. Yu, R. N. Richey, J. R. Stout, M. A. LaPack, R. Gu, V. V. Khau, S. A. Frank, J. P. Ott, R. D. Miller, M. A. Carr, T. Y. Zhang, Org. Process Res. Dev. 2008, 12, 218.
21. L. C. Blaszczak, B. M. Mathes, S. R. Pulley, M. A. Robertson, S. M. Sheehan, Q. Shi, B. M. Watson, M. R. Wiley, (Eli Lilly and Company), WO 015 767, 2007.
22. B. Allison, V. K. Phuong, M. C. W. Pippel, M. H. Rabinowitz, H. Venkatesan, (Janssen Pharmaceutica N. V.), U.S. 0,069,286, 2006
23. J. Liu, X. Deng, A. E. Fitzgerald, Z. S. Sales, H. Venkatesan, N. S. Mani, Org. Biomol. Chem. 2011, 9, 2654.
24. M. Pippel, K. Boyce, H. Venkatesan, V. K. Phuong, W. Yan, T. D. Barrett, G. Lagaud, L. Li, M. F. Morton, C. Prendergast, X. Wu, N. P. Shankley, M. H. Rabinowitz, Bioorg. Med. Chem. Lett. 2009, 19, 6376.
25. See, C. E. Humphrey, M. Furegati, K. Laumen, L. La Vecchia, T. Leutert, J. C. D. Mueller-Hartwieg, M. Voegtle, Org. Process Res. Dev. 2007, 11, 1069, and references therein.
26. M. T. Burger, D. Bussiere, J. Murray, S. Ng, Z.-J. Ni, K. B. Pfister, A. S. Wagman, Y. Zhou, (Chiron Corporation), WO 001406, 2007.
27. K. C. Nicolaou, T. Ohshima, F. Murphy, S. Barluenga, J. Xu, N. Winssinger, Chem. Commun. 1999, 809
28. K. C. Nicolaou, F. Murphy, S. Barluenga, T. Ohshima, H. Wei, J. Xu, D. L. F. Gray, O. Baudoin, J. Am. Chem. Soc. 2000, 122, 3830.
29. P. V. Chaturvedula, L. Chen, R. Civiello, A. P. Degnan, G. M. Dubowchik, X. Han, X. J. J. Jiang, J. E. Macor, G. S. Poindexter, G. O. Tora, G. Luo, US 0149503, 2007
30. X. Han, R. L. Civiello, H. Fang, D. Wu, Q. Gao, P. V. Chaturvedula, J. E. Macor, G. M. Dubowchik, J. Org. Chem. 2008, 73, 8502.
31. J. Y. Cha, G. L. Burnett, Y. Huang, J. B. Davidson, T. R. R. Pettus, J. Org. Chem. 2011, 76, 1361.
32. T. Kuroita, T. Oda, Y. Asano, N. Taya, K. Iwanaga, H. Tokuhara, Y. Fukase, (Takeda Pharmaceutical Company Limited), WO 139941, 2008.
33. J. Surtees, V. Marmon, E. Differding, V. Zimmermann, (Ucb Farchim S.A.), WO 064637, 2001
34. C. Ates, J. Surtees, A.-C. Burteau, V. Marmon, E. Cavoy, (UCB, S.A.), WO 014080, 2003
35. B. M. Kenda, A. C. Matagne, P. E. Talaga, P. M. Pasau, E. Differding, B. I. Lallemand, A. M. Frycia, F. G. Moureau, H. V. Klitgaard, M. R. Gillard, B. Fuks, P. Michel, J. Med. Chem. 2004, 47, 530
36. J. Surtees, F. Lurquin, O. Diouf, (Ucb, S.A.), WO 028435, 2005.
37. N. Khiri, E. Bertrand, M.-J. Ondel-Eymin, Y. Rousselin, J. Bayardon, P. D. Harvey, S. Jugé, Organometallics 2010, 29, 3622.
38. D. Choi, J. P. Stables, H. Kohn, J. Med. Chem. 1996, 39, 1907
39. S. V. Andurkar, J. P. Stables, H. Kohn, Tetrahedron: Asymmetry 1998, 9, 3841
40. P. Morieux, J. P. Stables, H. Kohn, Bioorg. Med. Chem. 2008, 16, 8968.
41. A. Davies, M. Lamb, P. Lyne, P. Mohr, B. Wang, T. Wang, D. Yu, (Astrazeneca), WO 082392, 2006
42. J. M. Gozgit, G. Bebernitz, P. Patil, M. Ye, J. Parmentier, J. Wu, N. Su, T. Wang, S. Ioannidis, A. Davies, D. Huszar, M. Zinda, J. Biol. Chem. 2008, 283, 32334.
43. T. Wang, S. Ioannidis, L. Almeida, M. H. Block, A. M. Davies, M. L. Lamb, D. A. Scott, M. Su, H.-J. Zhang, M. Alimzhanov, G. Bebernitz, K. Bell, M. Zinda, Bioorg. Med. Chem. Lett. 2011, 21, 2958.
44. The Rh-mediated asymmetric hydrogenation of substrate S13 usually leads to moderate results in terms of conversion and enantioselectivity. For literature precedents, see, W. Zhang, X. Zhang, Angew. Chem. 2006, 118, 5641
45. Angew. Chem. Int. Ed. 2006, 45, 5515, and references therein.
46. See, G. B. Shinde, N. C. Niphade, S. P. Deshmukh, R. B. Toche, V. T. Mathad, Org. Process Res. Dev. 2011, 15, 455, and references cited therein for recent synthetic approaches towards cinacalcet.
47. K. Han, C. Kim, J. Park, M.-J. Kim, J. Org. Chem. 2010, 75, 3105
48. K. Arunkumar, M. Appi Reddy, T. Sravan Kumar, B. Vijaya Kumar, K. B. Chandrasekhar, P. Rajender Kumar, M. Pal, Beilstein J. Org. Chem. 2010, 6, 1174, and references therein.
49. I. D. Gridnev, M. Yasutake, N. Higashi, T. Imamoto, J. Am. Chem. Soc. 2001, 123, 5268.
50. P. J. Vankawala, N. Kolla, C. R. Elati, M. Sreenivasulu, K. A. Kumar, Y. Anjaneyulu, S. Venkatraman, A. Bhattacharya, V. T. Mathad, Synth. Commun. 2007, 37, 3439.
51. K. M. J. Brands, J. F. Payack, J. D. Rosen, T. D. Nelson, A. Candelario, M. A. Huffman, M. M. Zhao, J. Li, B. Craig, Z. J. Song, D. M. Tschaen, K. Hansen, P. N. Devine, P. J. Pye, K. Rossen, P. G. Dormer, R. A. Reamer, C. J. Welch, D. J. Mathre, N. N. Tsou, J. M. McNamara, P. J. Reider, J. Am. Chem. Soc. 2003, 125, 2129
52. K. M. J. Brands, S. W. Krska, T. Rosner, K. M. Conrad, E. G. Corley, M. Kaba, R. D. Larsen, R. A. Reamer, Y. Sun, F.-R. Tsay, Org. Process Res. Dev. 2006, 10, 109.
53. T. Matsuda, K. Tsuji, T. Kamitanaka, T. Harada, K. Nakamura, T. Ikariya, Chem. Lett. 2005, 34, 1102
54. K. Bogár, J.-E. Bäckvall, Tetrahedron Lett. 2007, 48, 5471.