Homogeneous rhodium(i)-catalyzed reductive aminations

Organic Preparations and Procedures International

Volumn 36, Issue 2, 2004, Pages 99-120

  Tararov, Vitali I ^a   Kadyrov, Renat ^b   Riermeier, Thomas H ^b   Dingerdissen, Uwe ^b   Börner, Armin ^a,c  

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

^b EVONIK INDUSTRIES AG   (Germany)

^c UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; ENAMINE; IMINE; NITROGEN DERIVATIVE; OXAZOLIDINE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; COMPARATIVE STUDY; ENANTIOSELECTIVITY; HYDROGENATION; RACEMIC MIXTURE; REDUCTION;

EID: 2442628165     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304940409355381     Document Type: Article

References (70)

1. H. Glaser, F. Moller, G. Pieper, R. Schroter, G. Spielberger and H. Soil, Amine, in Houben-Weyl, Methoden der Organischen Chemie, Miiller, E., Ed.; Thieme-Verlag: Stuttgart, 1957.
2. A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff and C. A. Shah, J. Org. Chem., 61, 3849 (1996)
3. P. N. Rylander, Catalytic Hydrogenation in Organic Synthesis, Academic Press: New York, 1979;
4. P. N. Rylander, Catalytic Hydrogenation over Platinum Metals, Academic Press: New York, 1967.
5. S. Nishimura, Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley: New York, 2001.
6. S. Nishimura, Homogeneous Hydrogenation, P. A. Chaloner, M. A. Esteruelas, F. Jo6 and L. A. Oro, Eds; Kluwer: Dordrecht, 1993.
7. J. J. Birtill, M. Chamberlain, J. Hall, R. Wilson and I. Costello, in Catalysis of Organic Reactions, F. E. Herkes, Ed.; Dekker: New York, 1998, p. 255.
8. S. Gomez, J. A. Peters and T. Maschmeyer, Adv. Synth. Catal., 344, 1037 (2002).
9. S. Gomez, J. A. Peters and T. Maschmeyer, Applied Homogenous Catalysis with Organometallic Compounds, B. Comils and W. A. Herrmann, Eds.; Vol. 1 and 2, VCH; Weinheim, 1996.
10. S. Gomez, J. A. Peters and T. Maschmeyer, Transition Metals for Organic Synthesis, M. Beller and C. Bolm, Eds.; Vol. 1 and 2, Wiley-VCH: Weinheim, 1998. Ref. 3c, p. 286.
11. V. I. Tararov, R. Kadyrov, T. H. Riermeier, J. Holz and A. Bomer, Tetrahedron: Asymmetry, 10, 4009 (1999).
12. K. Inoguchi, S. Sakuraba and K. Achiwa, Synlett, 169 (1992).
13. F. Spindler and H.-U. Blaser, Enantioselective Reduction of C/N Bonds and Enamines with Hydrogen, in Transition Metals for Organic Synthesis, M. Beller, M. Bolm, Eds., Wiley-VCH: Weinheim, 1998, Volume 2, p. 69.
14. C. J. Cobley and J. P. Henschke, Adv. Synth. Catal., 345, 195 (2003)
15. J. P. Cahill, A. P. Lightfoot, A. P. Goddard, J. Rust and P. J. Guiry, Tetrahedron: Asymmetry, 9, 4307 (1998)
16. P. Schnider, G. Koch, R. Pretot, G. Wang, F. M. Bohnen, C. Kruger and A. Pfaltz, Chem. Eur. J., 3, 887 (1997).
17. C. A. Willoughby and C. A. Buchwald, J. Am. Chem. Soc., 114, 7562 (1992).
18. M. Ringwald, R. Sturmer and H. H. Brintzinger, J. Am. Chem. Soc., 121, 1524 (1999).
19. Y. P. Ng Cheon Chan and J. A. Osborn, J. Am. Chem. Soc., 112, 9400 (1990).
20. F. Spindler, B. Pugin and B. Blaser, Angew. Chem. Int. Ed. Engl., 29, 558 (1990).
21. R. Sablong and J. A. Osbom, Tetrahedron: Asymmetry, 7, 3059 (1996).
22. D. Xiao and X. Zhang, Angew. Chem. Int. Ed., 40, 3425 (2001).
23. V.-b. Jiang, A. J. Minnaard, B. Hessen, B. L. Feringa, A. L. L. Duchateau, A. L. L. Andrein, J. A. F. Boogers and J. G. de Vries, Org. Lett., 5, 1503 (2003).
24. K. Tani, J.-I. Onouchi, T. Yamagata and Y. Kataoka, Chemistry Lett., 955 (1995).
25. T. Morimoto and T. Achiwa, Tetrahedron: Asymmetry 6, 2661 (1995).
26. G. Zhu and X. Zhang, Tetrahedron: Asymmetry, 9, 2415 (1998).
27. S. Vastag, J. Bakos, J. Toros, N. E. Takach, R. B. King, B. Heil and L. Marko, J. Mol. Catal., 22, 283 (1984).
28. G. Becalski, A. G. Cullen, M. D. Fryzuk, B. R. James, B. R. Kang and S. J. Rettig, Inorg. Chem., 30, 5002 (1991).
29. J. M. Buriak and J. A. Osbom, Organometallics, 15, 3161 (1996).
30. C. Lensink, E. Rijberg and J. G. de Vries, J. Mol. Cat. A: Chem., 116, 199 (1997).
31. M. J. Burk and J. E. Feaster, J. Am. Chem. Soc., 114, 6266 (1992).
32. F. Spindler and H.-U. Blaser, Adv. Synth. Catal., 343, 68 (2001).
33. R. Sablong and J. A. Osborn, Tetrahedron Lett., 37, 4937 (1996).
34. E. A. Broger, W. Burkart, M. Hennig, M. Scalone and R. Schmid, Tetrahedron: Asymmetry, 9, 4043 (1998).
35. E. Guiu, B. Munoz, S. Castilldn and C. Claver, Adv. Synth. Catal., 345, 169 (2003).
36. A. Martorell, C. Claver and E. Fernandez, Inorg. Chem. Commun., 3, 132 (2000).
37. T. Ohkuma, M. Kitamura and R. Noyori, in Catalytic Asymmetric Synthesis, I. Ojima, Ed.; Wiley-VCH: New York, 2000, p. 1.
38. M. J. Burk and F. Bienewald, in Transition Metals for Organic Synthesis, M. Beller and C. Bolm, Eds.; Wiley-VCH, Weinheim, 1998, Vol. 2, p. 13.
39. W. Tang and X. Zhang, Chem. Rev., 203, 3029 (2003).
40. K. Matsumura, H. Shimizu, T. Saito and H. Kumobayashi, Adv. Synth. Catal, 345, 180 (2003).
41. M. T. Reetz, G. Mehler, A. Meiswinkel and T. Sell, Tetrahedron Lett., 43, 7941 (2002).
42. W. Li, J. P. Waldkirch and X. Zhang, J. Org. Chem., 67, 7618 (2002).
43. M. van den Berg, R. M. Haak, A. J. Minnaard, A. H. M. de Vries, J. G. de Vries and B. L. Feringa, Adv. Synth. Catal., 344, 1003 (2002).
44. J. Halpem, in Asymmetric Synthesis, J. D. Morrison, Ed.; Academic Press, Orlando, 1985, p. 41.
45. N. E. Lee and S. L. Buchwald, J. Am. Chem. Soc., 116, 5985 (1994).
46. P. Eilbracht, L. Barfacker, C. Buss, C. Hollmann, B. E. Kitsos-Rzychon, C. L. Kranemann, T. Rische, R. Roggenbuck and A. Schmidt, Chem. Rev., 99, 3329 (1999).
47. V. I. Tararov, R. Kadyrov, T. H. Riermeier, J. Holz and A. Bomer, Tetrahedron Lett., 41, 2351 (2000).
48. M. A. Yurovskaya and A. V. Karchava, Tetrahedron: Asymmetry, 9, 3331 (1998).
49. V. I. Tararov, R. Kadyrov, T. H. Riermeier and A. Bomer, Adv. Synth. Catal, 344, 200 (2002).
50. N. Sakura, K. Ito and M. Sekiya, Chem. Pharm. Bull., 20, 1156 (1972).
51. A. Pohland, H. R. Sullivan and R. E. McMahon, J. Am. Chem. Soc., 66, 1442 (1957).
52. V. I. Tararov, R. Kadyrov, T. H. Riermeier and A. Bomer, Synthesis, 375 (2002).
53. V. I. Tararov, R. Kadyrov, A. Monsees, T. H. Riermeier and A. Bomer, Adv. Synth. Catal., 345, 239 (2003). Ref. 3c, p. 226.
54. T. Itoh, K. Nagata, A. Kurihara, M. Miyazaki and A. Ohsawa, Tetrahedron Lett., 43, 3105 (2002).
55. Y. Han and M. Chorev, J. Org. Chem., 64, 1972 (1999).
56. K. Miura, K. Ootsuka, S. Suda, H. Nishikori and A. Hosomi, Synlett, 1617 (2001).
57. M. Kitamura, D. Lee, S. Hayashi, S. Tanaka and M. Yoshimura, J. Org. Chem., 67, 8685 (2002).
58. Fine Chemicals through Heterogeneous Catalysis, A. S. Sheldon and H. van Bekkum, Eds.; Wiley-VCH: Weinheim, 2001, p. 384.
59. L. Marko and J. Bakos, J. Organomet. Chem., 81, 411 (1974).
60. M. V. Klyuev and M. L. Khidekel, Transition Met. Chem., 5, 134 (1980).
61. M. Murakami and J.-W. Kang, Bull. Chem. Soc. Jpn, 36, 763 (1963).
62. R. Margalef-Catalh, C. Claver, P. Salagre and E. Fernandez, Tetrahedron Lett., 41, 6583 (2000).
63. V. I. Tararov, R. Kadyrov, T. H. Riermeier and A. Bomer, Chem. Commun., 1867 (2000).
64. H.-U. Blaser, H.-P. Buser, H.-P. Jalett, B. Pugin and F. Spindler, Synlett, 867 (1999).
65. Y. Chi, Y.-G. Zhou and X. Zhang, J. Org. Chem., 68, 4120 (2003).
66. R. Kadyrov and T. H. Riermeier, Angew. Chem. Lnt. Ed., 42, 5472 (2003).
67. G. D. Williams, R. A. Pike, C. E. Wade and M. Wills, Org. Lett., 5, 4227 (2003).
68. R. Aldea and H. Alper, J. Organomet. Chem., 593-594, 454 (2000).
69. R. Kadyrov, T. H. Riermeier, U. Dingerdissen, V. Tararov and A. Bomer, J. Org. Chem., 68, 4067 (2003).
70. V. I. Tararov, R. Kadyrov, T. H. Riermeier, C. Fischer and A. Bomer, Adv. Synth. Catal., (2004), In press.