Brønsted acid-catalyzed addition and cyclization reaction with imine: From aqueous reaction to enantioselective reactions

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 63, Issue 11, 2005, Pages 1062-1068

  Akiyama, Takahiko ^a   Fuchibe, Kohei ^a   Itoh, Junji ^a,b  

^a GAKUSHUIN UNIVERSITY   (Japan)

^b JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; CATALYST ACTIVITY; ORGANIC SOLVENTS; PHOSPHORIC ACID; REACTION KINETICS; SOLUTIONS;

ALDIMINES; CYCLIZATION REACTION;

ORGANIC ACIDS;

EID: 31444445303     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.63.1062     Document Type: Article

References (88)

1. Santelli, M.; Pons, J.-M. Lewis acids and Selectivity in Organic Synthesis, CRC Press, New York, 1996.
2. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Eds. Comprehensive Asymmetric Synthesis, Vol. I, II, III, Springer, Berlin, 1999.
3. (b) Tye, H.; Comina, P. J. J. Chem. Soc., Perkin Trans. 1 2001, 1729.
4. For selected examples of Brønsted acid-catalyzed carbon-carbon bond formations, see; (a) Park, J.-Y.; Kadota, I.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4901.
5. (b) Ishihara, K.; Hasegawa, A.; Yamamoto, H. Angew. Chem., Int. Ed. 2001, 40, 4077.
6. (c) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204.
7. For reviews on organic reactions in aqueous media, see; (a) Li, C.-J. Chem. Rev. 1993, 93, 2023.
8. (b) Li, C.-J.; Chan, T.-H. Organic Reactions in Aqueous Media, John Wiley, New York, 1997.
9. (c) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis, 1994, 741.
10. (d) Li, C.-J. Tetrahedron 1996, 52, 5643.
11. (e) Grieco, P. Ed. Organic Reactions in Water, Blackie Academic & Professional: London, 1998.
12. (f) Modern Solvents In Organic Synthesis (Topics In Current Chemistry, 206) Knochel, P.; Houk, K. N.; Kessler, H. Eds. Springer Verlag, Berlin, 1999.
13. (g) Lindstrom, U. M. Chem. Rev. 2002, 102, 2751.
14. Akiyama, T.; Iwai, J. Synlett 1998, 273.
15. Kobayashi, S.; Nagayama, S. J. Org. Chem. 1997, 62, 232.
16. Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1997, 119, 10049.
17. Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641.
18. Akiyama, T.; Takaya, J.; Kagoshima, H. Chem. Lett. 1999, 947.
19. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th Ed. John Wiley & Sons, New York 1988, p 174.
20. Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1045.
21. Akiyama, T.; Takaya, J.; Kagoshima, H. Synlett 1999, 1426.
22. Please see also, Manabe, K.; Mori, Y.; Kobayashi, S. Synlett 1999, 1401.
23. Akiyama, T.; Takaya, J.; Kagoshima, H. Tetrahedron Lett. 2001, 42, 4025.
24. Akiyama, T.; Matsuda, K.; Fuchibe, K. Synlett 2005, 322.
25. Please see also, Manabe, K.; Kobayashi, S. Org. Lett. 1999, 1, 1965.
26. Manabe, K.; Mori, Y.; Kobayashi, S. Tetrahedron 2001, 57, 2537.
27. Wu, Y.-S.; Cai, J.; Hu, Z.-Y; Lin, G.-X. Tetrahedron Lett. 2004, 45, 8949.
28. Akiyama, T.; Takaya, J.; Kagoshima, H. Tetrahedron Lett. 1999, 40, 7831.
29. Akiyama, T.; Sanada, M.; Fuchibe, K. Synlett 2003, 1463.
30. Akiyama, T.; Nakashima, S.; Yokota, K.; Fuchibe, K. Chem. Lett. 2004, 33, 922.
31. Wilen, S. H.; Qi, J. Z. J. Org. Chem. 1991, 56, 487.
32. Inanaga, J.; Sugimoto, Y.; Hanamoto, T. New J. Chem. 1995, 19, 707.
33. Furuno, H.; Hanamoto, T.; Sugimoto, Y.; Inanaga, J. Org. Lett. 2000, 2, 49.
34. For reviews, see; (a) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
35. (b) Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed, 2004, 43, 5138.
36. (c) Houk, K. N.; List, B. Eds. special issue on organocatalysis, Acc. Chem. Res. 2004, 37, 487.
37. (d) List, B.; Bolm, C. Eds. special issue on organocatalysis, Adv. Synth. Cat. 2004, 346, 1021.
38. (e) Berkessel, A.; Gröger, H. Eds. Asymmetric Organocatalysis, Wiley-VCH, Weinheim, 2005.
39. (f) Seayad, J.; List, B. Org. Biomol Chem. 2005, 3, 719.
40. (a) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279.
41. (b) Wenzel, A. G.; Jacobsen, E. N. J. Am, Chem. Soc. 2002, 124, 12964.
42. (c) Joly, G. D.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 4102.
43. (d) Fuerst, D. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 8964. See also
44. (e) Okino, T.; Hoashi, Y.; Takemoto, Y. J. Am. Chem. Soc. 2003, 125, 12672.
45. (f) Sohtome, Y.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Tetrahedron Lett. 2004, 45, 5589.
46. (g) Okino, T.; Nakamura, S.; Furukawa, T.; Takemoto, Y. Org. Lett. 2004, 6, 625.
47. (h) Hoashi, Y.; Yabuta, T.; Takemoto, Y. Tetrahedron Lett. 2004, 45, 9185.
48. (a) Huang, Y.; Unni, A. K.; Thadani, A. N.; Rawal, V. H. Nature 2003, 424, 146.
49. (b) Thadani, A. N.; Stankovic, A. R.; Rawal, V. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5846.
50. (c) Unni, A. K.; Takenaka, N.; Yamamoto, H.; Rawal, V. H. J. Am. Chem. Soc. 2005, 127, 1336.
51. For other recent representative papers, see; (a) McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094.
52. (b) Nugent, B. M.; Yoder, R. A.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 3418.
53. (c) McDougal, N. T.; Trevellini, W. L.; Rodgen, S. A.; Kliman, L. T.; Schaus, S. E. Adv. Synth. Catal. 2004, 346, 1231.
54. (d) Pihko, P. M. Angew. Chem., Int. Ed. 2004, 43, 2062.
55. (e) Du, H.; Zhao, D.; Ding, K. Chem. Eur. J. 2004, 10, 5964.
56. (f) Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 1080-1081.
57. Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566.
58. For selected examples of metal-catalyzed enantioselective Mannich and Mannich-type reactions, see; (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
59. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
60. (c) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180.
61. (d) Kobayashi, S.; Hamada, T.; Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640.
62. (e) Hagiwara, E.; Fujii, A.; Sodeoka, M. J. Am. Chem. Soc. 1998, 120, 2474.
63. (f) Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem., Int. Ed. 2001, 41, 2271.
64. (g) Ferraris, D.; Young, B.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 1998, 120, 4548.
65. (h) Taggi, A. E.; Hafez, A. M.; Lectka, T. Acc. Chem. Res. 2003, 36, 10.
66. (i) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
67. (j) Hamada, T.; Manabe, K.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 7768.
68. (k) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem. Int. Ed. 2005, 44, 1525.
69. For selected examples organo-catalyzed enantioselective Mannich and Mannich-type reactions, see: (a) List, B. J. Am. Chem. Soc. 2000, 122, 9336.
70. (b) Hayashi, Y.; Tsuboi, W.; Ashimine, I.; Urushima, T.; Shoji, M.; Sakai, K. Angew. Chem., Int. Ed. 2003, 42, 3677.
71. (c) Cordova, A. Acc. Chem. Res. 2004, 37, 102.
72. (d) Chowdari, N. S.; Suri, J. T.; Barbas III, C. F., Org. Lett. 2004, 6, 2507.
73. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
74. Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2004, 126, 11804.
75. Uraguchi, D.; Sorimachi, K.; Terada, M. J. Am. Chem. Soc. 2005, 127, 9360.
76. Wipf, P.; Jung, J.-K. J. Org. Chem. 2000, 65, 6319.
77. Akiyama, T.; Morita, H.; Itoh, J.; Fuchibe, K. Org. Lett. 2005, 7, 2583.
78. For selected examples of metal-catalyzed hydrophosphonylation reactions, see; (a) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656.
79. (b) Groeger, H.; Saida, Y.; Arai, S.; Martens, J.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 9291.
80. (c) Groger, H.; Saida, Y.; Sasai, H.; Yamaguchi, K.; Martens, J.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 3089.
81. (d) Saida, Y.; Gröger, H.; Maison, W.; Durot, N.; Sasai, H.; Shibasaki, M.; Martens, J. J. Org. Chem. 2000, 65, 4818.
82. (e) Kobayashi, S.; Kiyohara, H.; Nakamura, Y.; Matsubara, R. J. Am. Chem. Soc. 2004, 126, 6558.
83. For organo-catalyed hydrophosphonylation, see; lit. 20c.
84. Akiyama, T.; Itoh, J.; Tamura, Y.; Fuchibe, K. unpublished results.
85. Akiyama, T.; Saitoh, Y.; Morita, H.; Fuchibe, K. Adv. Synth. Catal. 2005, 347, 1523.
86. A number of conformers of the complex derived from phosphoric acid 1c and the imine were generated manually and were minimized by Spartan '02 (Wavefuncion, Inc) at the PM3 level.
87. For the bifunctional Lewis acids, see; Shibasaki, M.; Kanai, M.; Funabashi, K. Chem. Commun. 2002, 1989.
88. Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491.