Chiral zirconium catalysts using multidentate BINOL derivatives for catalytic enantioselective Mannich-type reactions; ligand optimization and approaches to elucidation of the catalyst structure

Journal of the American Chemical Society

Volumn 127, Issue 44, 2005, Pages 15528-15535

  Ihori, Yoichi ^a   Yamashita, Yasuhiro ^a   Ishitani, Haruro ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; DERIVATIVES; PROTEINS; SILICON; ZIRCONIUM;

ASSYMETRIC INDUCTION; BINOL DERIVATIVES; CHIRAL ZIRCONIUM CATALYSTS; MANNICH-TYPE REACTIONS;

CATALYSTS;

2,2' DIHYDROXY 1,1' BINAPHTHYL; 2,2' DIHYDROXY 1,1' BINAPHTHYL DERIVATIVE; UNCLASSIFIED DRUG; ZIRCONIUM;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; MANNICH REACTION; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 27644506699     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja053524d     Document Type: Article

References (71)

1. (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley-VCH: New York, 2000.
2. (b) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer: Heidelberg, 1999.
3. Yamamoto, H., Ed. Lewis Acids in Organic Synthesis; Wiley-VCH: Weinheim, 2000; Vol. 2.
4. Recent review of modified BINOL ligands in asymmetric catalysis: (a) Brunei, J. M. Chem. Rev. 2005, 105, 857.
5. (b) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
6. (a) Harada, S.; Handa, S.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 4365.
7. (b) Yoshida, T.; Morimoto, H.; Kumagai, N.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2005, 44, 3470.
8. (c) Matsunaga, S.; Yoshida, T.; Morimoto, H.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8777.
9. (d) Guo, H.; Wang, X.; Ding, K. Tetrahedron Lett. 2004, 45, 2009.
10. (e) Harada, T.; Hiraoka, Y.; Kusukawa, T.; Marutani, Y.; Matsui, S.; Nakatsugawa, M.; Kanda, K. Org. Lett. 2003, 5, 5059.
11. (f) Majima, K.; Takita, R.; Okada, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 15837.
12. (g) Harada, S.; Kumagai, N.; Kinoshita, T.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2582.
13. (h) Kumagai, N.; Matsunaga, S.; Kinoshita, T.; Harada, S.; Okada, S.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2169.
14. (i) Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibasaki, M. Org. Lett. 2001, 3, 1539.
15. (j) Yoshikawa, N.; Shibasaki, M. Tetrahedron 57, 2569.
16. (k) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506.
17. (l) Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 1561.
18. Reviews: (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
19. (b) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Ed.; Springer, Berlin, 1999; p 923.
20. (c) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
21. (d) Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; VCH: Weinheim, 1997.
22. (e) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Chapter 2.3, Vol. 2, p 893.
23. (a) Kobayashi, S.; Ueno, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, 1999; supplement 1, p 143.
24. For recent examples using silicon enolates, see also: (b) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734.
25. (c) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
26. (d) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507.
27. (e) Jaber, N.; Carrée, F.; Fiaud, J.-C; Collin, J. Tetrahedron: Asymmetry 2004, 14, 2067.
28. (f) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
29. Recently, several direct asymmetric Mannich-type reactions have been reported. For direct Mannich-type reactions, see reviews: (a) Córdova, A. Acc. Chem. Res. 2004, 37, 102.
30. For recent examples, see also: (b) Cobb, A. J. L.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84.
31. (c) Notz, W.; Watanabe, S.; Chowdari, N. S.; Zhong, G.; Betancort, J. M.; Tanaka, F.; Barbas, C. F., III Adv. Synth. Catal. 2004, 346, 1131.
32. (d) Ibrahem, I.; Casas, J.; Córdova, A. Angew. Chem., Int. Ed. 2004, 43, 6528.
33. (e) Zhuang, W.; Saaby, S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2004, 43, 4476.
34. (f) Matsunaga, S.; Yoshida, T.; Morimoto, H.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8777.
35. (g) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem. 2003, 115, 3805;
36. Angew. Chem., Int. Ed. 2003, 42, 3677.
37. (h) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J. Am. Chem. Soc. 2003, 125, 11208.
38. (i) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
39. (j) Watanabe, S.; Córdova, A.; Tanaka, F.; Barbas, C. F., III. Org. Lett. 2002, 4, 4519.
40. (k) Córdova, A.; Barbas, C. F., III. Tetrahedron Lett. 2002, 43, 7749.
41. (l) Córdova, A.; Watanabe, S.; Tanaka, F.; Notz, W.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1866.
42. (m) Córdova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F., III. J. Am. Chem. Soc. 2002, 124, 1842.
43. (n) List, B.; Porjaliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
44. (o) List, B. J. Am. Chem. Soc. 2000, 122, 9336.
45. For examples using modified esters, see: (p) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583.
46. (q) Marigo, M.; Kjsersgaard, A.; Juhl, K.; Gathergood, N.; Jørgensen, K. A. Chem.-Eur. J. 2003, 9, 2359.
47. (r) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356 and references therein.
48. Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
49. (a) Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161.
50. BBM was synthesized by Shibasaki's group independently: (b) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998. 39, 7917.
51. (c) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252.
52. Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253.
53. Diarylmethanols were also prepared by reactions of (R)-3-CHO-MOM-BINOL with ArLi or ArMgX.
54. Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180.
55. Very recently we reported the chiral niobium catalyst using tridentate BINOL derivative 6e for the Mannich-type reaction: Kobayashi, S.; Arai, K.; Shimizu, H.; Ihori, Y.; Ishitani, H.; Yamashita, Y. Angew. Chem., Int. Ed. 2005, 44, 761.
56. 6. When phenol was added to the Zr catalyst (Table 4, entry 3), it appeared at 159.1 ppm.
57. 1H NMR of complexes (a) and (c) in Figure 3 were measured in the presence of hexamethylbenzene as an internal standard, it was observed that the amount of complex A was decreased alone. The amounts of complex B and C did not change at all in these cases.
58. (a) Kagan, H. B. Synlett 2001, 888.
59. (b) Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. 1998, 37, 2923.
60. 1H NMR experiments.
61. TITAN, version 1.0; Wavefunction, Inc., Schrödinger, Inc., 1999.
62. JAGUAR, version 3.5; Schrödinger, Inc., 1998.
63. Halgren, T. A. J. Comput. Chem. 1996, 17, 490.
64. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
65. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
66. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
67. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
68. (a) Becke, A. D. J. Chem. Phys. 1992, 96, 2155-2166.
69. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
70. (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
71. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B41, 785.