Enantioselective hydrogenation with self-assembling rhodium phosphene catalysts: Influence of ligand structure and solvent

Chemistry - A European Journal

Volumn 13, Issue 20, 2007, Pages 5896-5907

  Birkholz, Mandy Nicole ^a   Dubrovina, Natalia V ^a   Jiao, Haijun ^a   Michalik, Dirk ^a   Holz, Jens ^a   Paciello, Rocco ^b   Breit, Bernhard ^c   Börner, Armin ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b BASF SE   (Germany)

^c UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Asymmetric catalysis; Density functional calculations; Drogenation; P ligands; Rhodium

Indexed keywords

CATALYSIS; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; HYDROGENATION; LIGANDS; METAL COMPLEXES;

ASYMMETRIC CATALYSIS; DROGENATION; ENANTIOSELECTIVE HYDROGENATION; P LIGANDS;

RHODIUM COMPOUNDS;

EID: 34547184437     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601607     Document Type: Article

References (82)

1. J.M. Brown in Comprehensive Asymmetric Catalysis, Vol. I (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 121-182;
2. T. Ohkuma, M. Kitamura, R. Noyori in Catalytic Asymmetric Synthesis (Ed.: I. Ojima), Wiley, New York, 2000, pp. 1-110;
3. H.-U. Blaser, B. Pugin, F, Spindler, J. Mol. Catal. A 2005, 231, 1-20.
4. For recent reviews, see: M. Diéguez, O. Pàmies, A. Ruiz, Y. Diaz, S. Castillón, C. Claver, Coord. Chem. Rev. 2004, 245, 2165-2192;
5. T. T.L. Au-Yueng, A. S. C Chan, Coord. Chem. Rev. 2004, 248, 2151-2164;
6. P. Barbara, C. Bianchini, G. Giambastiani, S. L. Parisel, Coord. Chem. Rev. 2004, 248, 2131-2150;
7. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069.
8. For reviews, see: F. Lagasse, H. B. Kagan, Chem. Pharm. Bull. 2000, 48, 315-324;
9. I.V. Komarov, A. Börner, Angew. Chem. 2001, 113, 1237-1239;
10. Angew. Chem. Int. Ed. 2001, 40, 1197-1200;
11. T. Jerphagnon, J.-L. Renaud, C. Bruneau, Tetrahedron: Asymmetry 2004, 15, 2101-2111.
12. For some recent results, see: B. Zhao, Z. Wang, K. Ding, Adv. Synth. Catal. 2006, 348, 1049-1057;
13. Q.-H. Zeng, X.-P. Hu, Z.-C. Duan, X.-M. Liang, Z. Zheng, J. Org. Chem. 2006, 77, 393-396;
14. H. Bernsmann, M. van den Berg, R. Hoen, A. X Minnaard, G. Mehler, M. T. Reetz, J. G. de Vries, B. L. Feringa, J. Org. Chem. 2005, 70, 943-951;
15. Y. Liu, K. Ding, J. Am. Chem. Soc. 2005, 127, 10488-10489;
16. S. Wu, W. Zhang, Z. Zhang, X. Zhang, Org. Lett. 2004, 6, 3565-3567.
17. Y. Liu, C. A. Sandoval, Y. Yamaguchi, X. Zhang, Z. Wang, K. Kato, K. Ding, J. Am. Chem. Soc. 2006, 128, 14212-14213;
18. K. Knight, Z. Freixa, P. W N. M. van Leeuwen, J. N. H. Reek, Organometallics 2006, 25, 954-960.
19. X.-B. Jiang, L. Lefort, P.E. Goudriaan, A. H. M. deVries, P. W. N. M. van Leeuwen, J. G. de Vries, J. N. H. Reek, Angew. Chem. 2006, 118, 1245-1249;
20. Angew. Chem. Int. Ed. 2006, 45,1223-1227;
21. J. M. Takacs, D. S. Reddy, S. A. Moteki, D. Wu, H. Palencia, J. Am. Chem. Soc. 2004, 126, 4494-4495;
22. J.M. Atkins, S.A. Moteki, S. G. DiMagno, J.M. Takacs, Org. Lett. 2006, 8, 2759-2762.
23. For reviews, see: M. J. Wilkinson, P. W. N. M. van Leeuwen, J. N. H. Reek, Org. Biomol. Chem. 2005, 3, 2371-2383;
24. S. X Reyes, K. Burgess, Chem. Soc. Rev. 2006, 35, 416-423;
25. A. W. Kleij, J. N. H. Reek, Chem. Eur. J. 2006, 12, 4218-4272.
26. a) B. Breit, W. Seiche, J. Am. Chem. Soc. 2003, 125, 6608-6609;
27. b) B. Breit, W Seiche, Pure Appl. Chem. 2006, 78, 249-256;
28. c) W. Seiche, A. Schuschkowski, B. Breit, Adv. Synth. Catal. 2005, 347, 1488-1494;
29. d) F. Chevallier, B. Breit, Angew. Chem. 2006, 118, 1629-1632;
30. Angew. Chem. Int. Ed. 2006, 45, 1599-1602.
31. B. Breit, W. Seiche, Angew. Chem. 2005, 117, 1666-1669;
32. Angew. Chem. Int. Ed. 2005, 44, 1640-1643;
33. B. Breit, Angew. Chem. 2005, 117, 6976-6978;
34. Angew. Chem. Int. Ed. 2005, 44, 6816-6825.
35. M. Weis, C. Walloch, W. Seiche, B. Breit, J. Am. Chem Soc. 2006, 128, 4188-4189.
36. For reviews, see: T. P. Clark, C. R. Landis, Tetrahedron: Asymmetry 2004, 15, 2123-2213;
37. J. Holz, M.-N. Gensow, O. Zayas, A. Börner, Current Org. Chem. 2007, 11, 61-106.
38. a) M. J. Burk, J. E. Feaster, R. L. Harlow, Organometallics 1990, 9, 2653-2655;
39. b) M. J. Burk, J. E. Feaster, R. L. Harlow, Tetrahedron: Asymmetry 1991, 2, 569-592;
40. c) M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518-8519;
41. d) M. J. Burk, J. E. Feaster, W. A. Nugent, R. L. Harlow, J. Am. Chem. Soc. 1993, 115, 10125-10138.
42. a) F. Guillen, J.-C. Fiaud, Tetrahedron Lett. 1999, 40, 2939-2942;
43. b) F. Guillen, M. Rivard, M. Toffano, J.-C. Legros, J.-C. Fiaud, Tetrahedron 2002, 58, 5895-5904.
44. N. V. Dubrovina, H. Jiao, V. I. Tararov, A. Spannenberg, R. Kadyrov, A. Monsees, A. Christensen, A. Börner, Eur. J. Org. Chem. 2006, 3412-3420.
45. S. Gladiali, A. Dore, D. Fabbri, O. De Lucci, M. Manassero, Tetrahedron: Asymmetry 1994, 5, 511-514.
46. a) K. Junge, G. Oehme, A. Monsees, T. Riermeier, U. Dingerdissen, M Beller, Tetrahedron Lett. 2002, 43, 4977-4980;
47. b) K. Junge, B. Hagemann, S. Enthaler, G. Oehme, M. Michalik, A. Monsees, T. Riermeier, U. Dingerdissen, M. Beller, Angew. Chem. 2004, 116, 5176-5179;
48. Angew. Chem. Int. Ed. 2004, 43, 5066-5069;
49. c) K. Junge, B. Hagemann, S. Enthaler, A. Spannenberg, M. Michalik, G. Oehme, A. Monsees, T Riermeier, M. Beller, M. Tetrahedron: Asymmetry 2004, 15, 2621-2631;
50. d) B. Hagemann, K. Junge, S. Enthaler, M. Michalik, T. Riermeier, A. Monsees, B. Beller, Adv. Synth. Catal. 2005, 347,1978-1986;
51. e) S. Enthaler, B. Hagemann, K. Junge, G. Erre, M. Beller, Eur. J. Org. Chem. 2006, 2912-2917.
52. For other applications of phosphepines, see: J. E. Wilson, G. C Fu, Angew. Chem. 2006, 118, 1454-1457;
53. Angew. Chem. Int. Ed. 2006, 45, 1426-1429.
54. D. Xiao, Z. Zhang, X. Zhang, Org. Lett. 1999, 1, 1679-1681.
55. L. Shi, X. Wang, C A. Sandoval, M. Li, Q. Qi, Z. Li, K. Ding, Angew. Chem. 2006, 118, 4214-4218;
56. Angew. Chem. Int. Ed. 2006, 45, 4108-4112;
57. P.A. Duckmanton, A.J. Blake, J.B. Love, lnorg. Chem. 2005, 44, 7708-7710.
58. IR spectroscopic investigations in solution were not successful due to fast decomposition of the free ligands in aerobic solvents.
59. a) C. B. Fischer, H. Steininger, D. S. Stephenson, H. Zipse, J. Phys. Org. Chem. 2005, 18, 901-907;
60. b) P. L. Wash, E. Maverick, J. Chiefari, D. A. Lightner, J. Am. Chem. Soc. 1997, 119, 3802-3806;
61. c) M. Gallant, M. T. Phan Viet, X D. Wuest, J. Am. Chem. Soc. 1991, 113, 721-723.
62. 3OD showed a broad singlet at δ = 49.7 ppm indicating equivalence of the two phosphorus atoms due to cleavage of the hydrogen bonds.
63. 3 some minor species were found with resonances between δ = - 9 and - 15 ppm. This may indicate the formation of P,N-coordinated mononuclear or binuclear species.
64. 3 no P,P coupling was observed.
65. These data correlate well with those of related cis and trans Pt complexes: D. W. W. Anderson, E. A. V. Ebsworth, D. W. H. Rankin, J. Chem. Soc. Dalton 1973, 2370-2373.
66. P. Beak, Ace. Chem. Res. 1977, 10, 186-192,
67. and references therein; A. Dkhissi, R. Ramaekers, L. Houben, L. Adamowicz, G. Maes, Chem. Phys. Lett. 2000, 331, 553-560;
68. Forlani, G. Cristoni, C. Boga, P. E. Todesco, E. Del Vecchio, S. Selva, M. Monari, ARKIVOC 2002, 11, 198-215;
69. J.A. Frey, S. Leutwyler, Chimia 2005, 59, 511-516.
70. M. Piacenza, S. Grimme, J. Comput. Chem. 2004, 25, 83-98.
71. P.-T. Chou, C-Y. Wie, F-T. Hung, J. Phys. Chem. B 1997, 707, 9119-9126.
72. M. W. Wong, K. B. Wiberg, M. J. Frisch, J. Am. Chem. Soc. 1992, 774, 1645-1652, and references therein.
73. a) T. Gronneberg, K. Undheim, Tetrahedron Lett 1972, 73, 3193-3196;
74. b) A. Maquestian, Y. van Haverbeke, C de Meyer, A. R. Katritzky, M. X Cook, A. D. Page, Can. J. Chem. 1975, 53, 490-496.
75. P. Beak, F. S. Fry, J Am. Chem. Soc. 1973, 95,1700-1702.
76. a) M. J. Nowak, L. Lapinski, J. Fulara, A, Les, L. Adamowicz, J. Phys. Chem. 1992, 96, 1562-1569;
77. b) L.D. Hatherley, R. D. Brown, P. D. Godfrey, A. P. Pierlot, W. Caminati, D. Damiani, S. Melandri, L. B. Favero, J. Phys. Chem. 1993, 97, 46-51.
78. Gaussian 03, Revision C.02, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G. E. Scuseria, M. A. Robb, X R. Cheeseman, X A. Montgomery, Jr., T, Vreven, K. N. Kudin, X C. Burant, X M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, X Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, X E. Knox, H. P. Hratchian, J. B. Cross, C Adamo, X Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. X Austin, R. Cammi, C Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. X Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M. C Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, X B. Foresman, J.V., Ortiz, Q. Cui, A. G. Baboul, S. Clifford, X Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W Chen, M.W. Wong, C Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford, CT, 2004.
79. [19]
80. J. Sakaki, W. B. Schweizer, D. Seebach, Helv. Chim. Acta 1993, 76, 2654-2665.
81. S. Choppin, F. Gros, Y. Fort, Org. Lett. 2000, 2, 803-805.
82. H. Nöth, H.-J. Vetter, Chem. Ber. 1963, 96, 1109-1118.