Synthesis of amidolanthanides with new chiral biaryl-based NNO ligands and their use as catalysts for enantioselective hydroamination/cyclization

Inorganic Chemistry

Volumn 47, Issue 10, 2008, Pages 4319-4328

  Wang, Qiuwen ^a   Xiang, Li ^a   Song, Haibin ^b   Zi, Guofu ^a  

^a BEIJING NORMAL UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

LANTHANIDE; LIGAND; NITRIC OXIDE; NITROGEN;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROGENATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINATION; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HYDROGENATION; LANTHANOID SERIES ELEMENTS; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRIC OXIDE; NITROGEN; STEREOISOMERISM;

EID: 44349162907     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic702461f     Document Type: Article

References (75)

1. (a) For general hydroamination reviews, see: Odom, A. L. Dalton Trans. 2005, 225-233.
2. (b) Doye, S. Synlett 2004, 1653-1672.
3. (c) Pohlki, F.; Doye, S. Chem. Soc. Rev. 2003, 32, 104-114.
4. (d) Bytschkov, I.; Doye, S. Eur. J. Org. Chem. 2003, 935-946.
5. (e) Seayad, J.; Tillack, A.; Hartung, C. G.; Beller, M. Adv. Synth. Catal. 2002, 344, 795-813.
6. (f) Nobis, M.; Driessen-Hölscher, B. Angew. Chem., Int. Ed. 2001, 40, 3983-3985.
7. (g) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-704.
8. (a) For reviews of asymmetric hydroamination, see: Roesky, P. W.; Müller, T. E. Angew. Chem., Int. Ed. 2003, 42, 2708-2710.
9. (b) Hong, S.; Marks, T. J. Acc. Chem. Res. 2004, 37, 673-686.
10. (c) Hultzsch, K. C. Org. Biomol. Chem. 2005, 3, 1819-1824.
11. (d) Hultzsch, K. C. Adv. Synth. Catal. 2005, 347, 367-391.
12. (e) Hii, K. K. Pure Appl. Chem. 2006, 78, 341-349.
13. (f) Aillaud, I.; Collin, J.; Hannedouche, J.; Schulz, E. Dalton Trans. 2007, 5105-5118.
14. (a) For selected papers for asymmetric hydroaminations using lanthanide metal catalysts with chiral Cp ligands, see: Gagné, M. R.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 275-294.
15. (b) Gagné, M. R.; Brard, L.; Conticello, V. P.; Giardello, M. A.; Stern, C. L.; Marks, T. J. Organometallics 1992, 11, 2003-2005.
16. (c) Giardello, M. A.; Conticello, V. P.; Brard, L.; Sabat, M.; Rheingold, A. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10241-10245.
17. (d) Vitanova, D. V.; Hampel, F.; Hultzsch, K. C. J. Organomet. Chem. 2007, 692, 4690-4701, and references therein.
18. Hong, S.; Tian, S.; Metz, M. V.; Marks, T. J. J. Am. Chem. Soc. 2003, 125, 14768-14783.
19. (a) O'Shaughnessy, P. N.; Knight, P. D.; Morton, C.; Gillespie, K. M.; Scott, P. Chem. Commun. 2003, 1770-1771.
20. (b) O'Shaughnessy, P. N.; Gillespie, K. M.; Knight, P. D.; Munslow, I. J.; Scott, P. Dalton Trans. 2004, 2251-2256.
21. Kim, J. Y.; Livinghouse, T. Org. Lett. 2005, 7, 1737-1739.
22. (a) Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748-3759.
23. (b) Gribkov, D. V.; Hultzsch, K. C. Chem. Commun. 2004, 730-731.
24. (c) Gribkov, D. V.; Hampel, F.; Hultzsch, K. C. Eur. J. Inorg. Chem. 2004, 4091-4101.
25. (d) Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. Chem. - Eur. J. 2003, 9, 4796-4810.
26. (e) Yu, X.; Marks, T. J. Organometallics 2007, 26, 365-376.
27. (f) Heck, R.; Schulz, E.; Collin, J.; Carpentier, J.-F. J. Mol. Catal. A: Chem. 2007, 268, 163-168.
28. (a) Riegert, D.; Collin, J.; Meddour, A.; Schulz, E.; Trifonov, A. J. Org. Chem. 2006, 71, 2514-2517.
29. (b) Collin, J.; Daran, J. C.; Jacquet, O.; Schulz, E.; Trifonov, A. Chem. - Eur. J. 2005, 11, 3455-3462.
30. (c) Collin, J.; Daran, J. C.; Schulz, E.; Trifonov, A. Chem. Commun. 2003, 3048-3049.
31. (d) O'Shaughnessy, P. N.; Scott, P. Tetrahedron: Asymmetry 2003, 14, 1979-1983.
32. (e) Meyer, N.; Zulys, A.; Roesky, P. W. Organometallics 2006, 25, 4179-4182.
33. (f) Riegert, D.; Collin, J.; Daran, J. C.; Fillebeen, T.; Schulz, E.; Lyubov, D.; Fukin, G.; Trifonov, A. Eur. J. Inorg. Chem. 2007, 1159-1168.
34. (g) Kim, H.; Kim, Y. K.; Shim, J. H.; Kim, M.; Han, M.; Livinghouse, T.; Lee, P. H. Adv. Synth. Catal. 2006, 348, 2609-2618.
35. (h) Aillaud, I.; Wright, K.; Collin, J.; Schulz, E.; Mazaleyrat, J.-P. Tetrahedron: Asymmetry 2008, 19, 82-92.
36. (i) Aillaud, I.; Collin, J.; Duhayon, C.; Guillot, R.; Lyubov, D.; Schulz, E.; Trifonov, A. Chem. - Eur. J. 2008, 14, 2189-2200.
37. (a) For asymmetric hydroamination using late transition metal catalysts, see: Löber, O.; Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 4366-4367.
38. (b) Paul, N. T.; Lutete, L. M.; Wu, H.; Pahadi, N. K.; Gridnev, I. D.; Yamamoto, Y. J. Org. Chem. 2006, 71, 4270-4279.
39. (c) Hu, A.; Ogasaware, M.; Sakamoto, T.; Okada, A.; Nakajima, K.; Takahashi, T.; Lin, W. Adv. Synth. Catal. 2006, 348, 2051-2056.
40. (d) LaLonde, R. L.; Sherry, B. D.; Kang, E. J.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2452-2453.
41. (e) Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. Org. Lett. 2007, 9, 2887-2889.
42. (f) Zhang, Z.; Bender, C. F.; Widenhoefer, R. A. J. Am. Chem. Soc. 2007, 129, 14148-14149.
43. (a) For examples of asymmetric hydroamination using other metal catalysts, see: Knight, P. D.; Munslow, I.; O'Shaughnessy, P. N.; Scott, P. Chem. Commun. 2004, 894-895.
44. (b) Gribkov, D. V.; Hultzcsh, K. C. Angew. Chem., Int. Ed. 2004, 43, 5542-5546.
45. (c) Martinez, P. H.; Hultzsch, K. C.; Hampel, F. Chem. Commun. 2006, 2221-2223.
46. (d) Watson, D. A.; Chiu, M.; Bergman, R. G. Organometallics 2006, 25, 4731-4733.
47. (e) Wood, M. C.; Leitch, D. C.; Yeung, C. S.; Kozak, J. A.; Schafer, L. L. Angew. Chem., Int. Ed. 2007, 46, 354-358.
48. (f) Gott, A. L.; Clarke, A. J.; Clarkson, G. J.; Scott, P. Organometallics 2007, 26, 1729-1737.
49. (g) Ogata, T.; Ujihara, A.; Tsuchida, S.; Shimizu, T.; Kaneshige, A.; Tomioka, K. Tetrahedron Lett. 2007, 48, 6648-6650.
50. (a) Zi, G.-F.; Yin, C.-L. Acta Chim. Sin. 1998, 56, 484-484.
51. (b) Zi, G.-F.; Yin, C.-L. J. Mol. Catal. A: Chem. 1998, 132, L1-L4.
52. (c) Zi, G.; Xiang, L.; Zhang, Y.; Wang, Q.; Yang, Y.; Zhang, Z. J. Organomet. Chem. 2007, 692, 3949-3956.
53. (d) Zhang, Z.; Li, M.; Zi, G. Chirality 2007, 19, 802-808.
54. (e) Zhang, Y.; Xiang, L.; Wang, Q.; Duan, X.-F.; Zi, G. Inorg. Chim. Acta 2008, 361, 1246-1254.
55. (f) Xiang, L.; Song, H.; Zi, G. Eur. J. Inorg. Chem. 2008, 1135-1140.
56. (a) Xiang, L.; Wang, Q.; Song, H.; Zi, G. Organometallics 2007, 26, 5323-5329.
57. (b) Zi, G.; Xiang, L.; Song, H. Organometallics 2008, 27, 1242-1246.
58. (a) For selected recent reviews, see: Shibasaki, M.; Yoshikawa, N. Chem. Rev. 2002, 102, 2187-2210.
59. (b) Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. L. Chem. Rev. 2002, 102, 2227-2302.
60. (c) Aspinall, H. C. Chem. Rev. 2002, 102, 1807-1850.
61. (d) Che, C.-M.; Huang, J.-S. Coord. Chem. Rev. 2003, 242, 97-113.
62. (e) Knight, P. D.; Scott, P. Coord. Chem. Rev. 2003, 242, 125-143.
63. (f) Kočovský, P.; VyskočilŠ.; Smrčina, M. Chem. Rev. 2003, 103, 3213-3246.
64. (g) Ding, K.; Li, X.; Ji, B.; Guo, H.; Kitamura, M. Curr. Org. Synth. 2005, 2, 499-545.
65. (h) Ding, K.; Guo, H.; Li, X.; Yuan, Y.; Wang, Y. Top. Catal. 2005, 35, 105-116.
66. (i) Brunel, J. M. Chem. Rev. 2005, 105, 857-898.
67. Wang, Q.; Xiang, L.; Zi, G. J. Organomet. Chem. 2008, 693, 68-76.
68. Liang, Y.; Gao, S.; Wan, H.; Wang, J.; Chen, H.; Zheng, Z.; Hu, X. Tetrahedron: Asymmetry 2003, 14, 1267-1273.
69. Guo, H.; Ding, K. Tetrahedron Lett. 2000, 41, 10061-10064.
70. Bradley, D. C.; Ghotra, J. S.; Hart, F. A. J. Chem. Soc., Dalton Trans. 1973, 1021-1023.
71. Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1996.
72. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure from Diffraction Data; University of Göttingen: Göttingen, Germany, 1997.
73. (a) Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080-1106.
74. (b) Ingold, C. K. J. Chem. Soc. 1921, 119, 305-329.
75. 2}phenylene. See: Yuen, H. F.; Marks, T. J. Organometallics 2008, 27, 155-158.