BINAP: Rhodium-diolefin complexes in asymmetric hydrogenation

Tetrahedron Asymmetry

Volumn 21, Issue 9-10, 2010, Pages 1226-1231

  Preetz, Angelika ^a   Drexler, Hans Joachim ^a   Schulz, Stefan ^a   Heller, Detlef ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 CYCLOOCTADIENE; 2,5 NORBORNADIENE; ALKADIENE; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; HYDROGENATION; MICHAELIS MENTEN KINETICS; PRIORITY JOURNAL; SYNTHESIS; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 77956660811     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.03.017     Document Type: Article

References (61)

1. W. Zhang, Y. Chi, and X. Zhang Acc. Chem. Res. 40 2007 1278 1290
2. D. Rivillo, H. Gulyás, J. Benet-Buchholz, E.C. Escudero-Adán, Z. Freixa, and P.W.N.M. van Leeuwen Angew. Chem., Int. Ed. 119 2007 7385 7388
3. Angew. Chem., Int. Ed. 46 2007 7247 7250
4. P.C.J. Kamer, P.W.N.M. van Leeuwen, and J.N.H. Reek Acc. Chem. Res. 34 2001 895 904
5. P.W.N.M. van Leeuwen, P.C.J. Kamer, J.N.H. Reek, and P. Dierkes Chem. Rev. 100 2000 2741 2769
6. P. Dierkes, and P.W.N.M. van Leeuwen J. Chem. Soc., Dalton Trans. 1999 1519 1529
7. A. Zanotti-Gerosa, W.A. Kinney, G.A. Grasa, J. Medlock, A. Seger, S. Ghosh, C.A. Telehab, and B.E. Maryanoff Tetrahedron: Asymmetry 19 2008 938 944
8. S.P. Smidt, N. Zimmermann, M. Studer, and A. Pfaltz Chem. Eur. J. 10 2004 4685 4693
9. J. van den Broeke, E. de Wolf, B.-J. Deelman, and G. van Koten Adv. Synth. Catal. 345 2003 625 635
10. A. Pfaltz, J. Blankenstein, R. Hilgraf, E. Hörmann, S. McIntyre, F. Menges, M. Schönleber, S.P. Smidt, B. Wüstenberg, and N. Zimmermann Adv. Synth. Catal. 345 2003 33 43
11. A. Rifat, N.J. Patmore, M.F. Mahon, and A.S. Weller Organometallics 21 2002 2856 2865
12. D.-R. Hou, J. Reibenspies, T.J. Colacot, and K. Burgess Chem. Eur. J. 7 2001 5391 5400
13. J.M. Buriak, J.C. Klein, D.G. Herrington, and J.A. Osborn Chem. Eur. J. 6 2000 139 150
14. A. Lightfoot, P. Schnider, and A. Pfaltz Angew. Chem. 110 1998 3047 3050
15. Angew. Chem., Int. Ed. 37 1998 2897 2899
16. D.J.R. OMahony, D.B. Belanger, and T. Livinghouse Synlett 1998 443 445
17. J.M. Buriak, and J.A. Osborn Organometallics 15 1996 3161 3169
18. T. Ohta, H. Ikegami, T. Miyake, and H. Takaya J. Organomet. Chem. 502 1995 169 176
19. J.C. Bayon, P. Esteban, J. Real, C. Claver, and A. Ruiz J. Chem. Soc., Dalton Trans. 1989 1579 1581
20. R. Selke J. Prakt. Chem. 329 1987 717 724
21. M. Berthod, G. Mignani, G. Woodward, and M. Lemaire Chem. Rev. 105 2005 1801 1836
22. R. Noyori Angew. Chem. 114 2002 2108 2123
23. Angew. Chem., Int. Ed. 41 2002 2008 2022 (Nobel lecture)
24. A. Miyashity, H. Takaya, T. Souchi, and R. Noyori Tetrahedron 8 1984 1245 1253
25. A. Miyashity, A. Yasuda, H. Takaya, K. Toriumi, and R. Noyori J. Am. Chem. Soc. 102 1980 7932 7934
26. K. Toriumi, T. Ito, H. Takaya, T. Souchi, and R. Noyori Acta Crystallogr., Sect. B 38 1982 807 812
27. R.R. Schrock, and J.A. Osborn J. Am. Chem. Soc. 93 1971 2397 2407
28. Crystallographic data (excluding structure factors) for the structures of 1-4 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 743810-743813. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: (internat.) +44 1223/336-033; e-mail: deposit@ccdc.cam.ac.uk ].
29. X. Zhang, K. Mashima, K. Koyano, N. Sayo, H. Kumobayashi, S. Akutagawa, and H. Takaya J. Chem. Soc., Perkin Trans. 1 1994 2309 2322
30. H.-J. Drexler, S. Zhang, A. Sun, A. Spannenberg, A. Arrieta, A. Preetz, and D. Heller Tetrahedron: Asymmetry 15 2004 2139 2150 Report 68
31. C.R. Landis, R.C. Nelson, W. Jin, and A.C. Bowman Organometallics 25 2006 1377 1391
32. C. Janiak J. Chem. Soc., Dalton Trans. 2000 3885 3896
33. X. Ye, Z.-H. Li, W. Wang, K. Fan, W. Xu, and Z. Hua Chem. Phys. Lett. 397 2004 56 61
34. W.L. Jorgensen, and D.L. Severance J. Am. Chem. Soc. 112 1990 4768 4774
35. E.P. Kyba, R.E. Davis, P.N. Juri, and K.R. Shirley Inorg. Chem. 20 1981 3616 3623
36. R.E. Davis, B.B. Meyer, K.L. Hassett, P.N. Juri, and E.P. Kyba Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 40 1984 21 24
37. S.K. Armstrong, J.M. Brown, and M.J. Burk Tetrahedron Lett. 34 1993 879 882
38. E. de Wolf, A.L. Spek, B.W.M. Kuipers, A.P. Philipse, J.D. Meeldijk, P.H.H. Bomans, P.M. Frederik, B.-J. Deelman, and G. van Koten Tetradedron 58 2002 3911 3922
39. H. Altinel, G. Avsar, and B. Guzel Transition Met. Chem. 34 2009 331 335
40. B. Guzel, M.A. Omary, J.P. Fackler Jr., and A. Akgerman Inorg. Chim. Acta 325 2001 45 50
41. A. Preetz, H.-J. Drexler, C. Fischer, Z. Dai, A. Börner, W. Baumann, A. Spannenberg, R. Thede, and D. Heller Chem. Eur. J. 14 2008 1445 1451
42. D. Heller, A.H.M. de Vries, and J.G. de Vries J.G. de Vries, C. Elsevier, Homogeneous Hydrogenation 2007 WILEY-VCH Weinheim 1483 1516
43. Pseudo rate constants still contain the hydrogen solubility under reaction conditions.
44. R. Noyori, and H. Takaya Acc. Chem. Res. 23 1990 345 350
45. For theoretical studies on the origin of the enantioselectivity with Rh/BINAP-complexes see: S. Mori, T. Vreven, and K. Morokuma Chem. Asian J. 1 2006 391 403
46. 2-bridging anion in such dimers do not necessarily have to be true counterion effects.
47. H.-J. Drexler, A. Preetz, T. Schmidt, and D. Heller J.G. de Vries, C.J. Elsevier, Handbook of Homogeneous Hydrogenation 2007 WILEY-VCH Weinheim 257 293
48. Murata, M.; Yamamoto, N.; Yoshikawa, K.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull. 1991, 10, 2767-2769 (An enantioselectivity of 15% at 42% conversion after 24 h at 10 atm and 50 °C in MeOH is observed).
49. M. Alame, N. Pestre, and C. de Bellefon Adv. Synth. Catal. 350 2008 898 908
50. M. Alame, M. Jahjah, S. Pellet-Rostaing, M. Lemaire, V. Meille, and C. de Bellefon J. Mol. Catal. A: Chem. 271 2007 18 24
51. M. Alame, M. Jahjah, M. Berthod, M. Lemaire, V. Meille, and C. de Bellefon J. Mol. Catal. A: Chem. 268 2007 205 212
52. J. Bayardon, J. Holz, B. Schäffner, V. Andrushko, S. Verevkin, A. Preetz, and A. Börner Angew. Chem. 119 2007 6075 6078
53. Angew. Chem., Int. Ed. 46 2007 5971 5974
54. The ee values for the MAC hydrogenations in other solvents have been published recently; S. Doherty, C.H. Smyth, A. Harriman, R.W. Harrington, and W. Clegg Organometallics 28 2009 888 895
55. A. Preetz, W. Baumann, C. Fischer, H.-J. Drexler, T. Schmidt, R. Thede, and D. Heller Organometallics 28 2009 3673 3677
56. D. Heller, H.-J. Drexler, A. Spannenberg, B. Heller, J. You, and W. Baumann Angew. Chem. 114 2002 814 817
57. Angew. Chem., Int. Ed. 41 2002 777 780
58. Rh = -967.2 ppm (Schmidt, T.; Baumann, W.; Heller, D. unpublished results).
59. C. Bianchini, P. Barbaro, V. Dal Santo, R. Gobetto, A. Meli, W. Oberhauser, R. Psaro, and F. Vizza Adv. Synth. Catal. 343 2001 41 45
60. P.N.M. Botman, J. Fraanje, K. Goubitz, R. Peschar, J.W. Verhoeven, J.H. van Maarseveen, and H. Hiemstra Adv. Synth. Catal. 346 2004 743 754
61. J.M. Hopkins, S.A. Dalrymple, M. Parvez, and B.A. Keay Org. Lett. 7 2005 3765 3768