Asymmetric reduction of aromatic ketimines in the presence of helical polymer as catalyst

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 47, Issue 19, 2009, Pages 4971-4981

  Kayo, Terada ^a   Toshio, Masuda ^b   Fumio, Sanda ^a  

^a KYOTO UNIVERSITY   (Japan)

^b FUKUI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

Catalysis; Chiral; Polyacetylenes

Indexed keywords

ASYMMETRIC REDUCTION; CHIRAL; ETHYNYL; GOOD YIELD; HELICAL POLYMERS; HELICAL STRUCTURES; KETIMINES; L-VALINE; NUMBER-AVERAGE; ONE-HANDED; OPTICALLY ACTIVE; RHODIUM CATALYSTS; UV-VIS SPECTRA;

ACETYLENE; AMINES; AROMATIC POLYMERS; CATALYSIS; CATALYSTS; POLYACETYLENES; RHODIUM;

POLYMERS;

EID: 69949166147     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.23549     Document Type: Article

References (111)

1. (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J Am. Chem. Soc 2000, 122, 2395-2396;
2. (b) Notz, W.; List, B. J Am Chem Soc 2000, 122, 7386-7387;
3. (c) List, B.; Pojarliev, P.; Castello, C. Org Lett 2001, 3, 573-575.
4. (a) List, B. J Am Chem Soc 2000, 122, 9336-9337;
5. (b) Hayashi, Y.; Tsuboi, W.; Shoji, M.; Suzuki, N. J Am Chem Soc 2003, 125, 11208-11209.
6. (a) List, B. J Am Chem Soc 2002, 124, 5656-5657;
7. (b) Bøgevig, A.; Juhl, K.; Kumaragurubaran, N.; Zhuang, W.; Jørgensen, K. A. Angew Chem. Int Ed 2002, 41, 1790-1793.
8. (a) Zhong, G. Angew Chem Int Ed 2003, 42, 4247-4250;
9. (b) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. G. J Am Chem Soc 2003, 125, 10808-10809;
10. (c) Bøgevig, A.; Súnden, H.; Córdova, A. Angew Chem Int Ed 2004, 43, 1109-1112;
11. (d) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Shoji, M. Angew Chem Int Ed 2004, 43, 1112-1115.
12. Northrup, A. B.; MacMillan, D. W. C. J Am Chem Soc 2002, 124, 6798-6799.
13. List, B.; Pojarliev, P.; Martin, H. J. Org Lett 2001, 3, 2423-2425.
14. (a) Zhao, Y.; Rodrigo, J.; Hoveyda, A. H.; Snapper, M. L. Nature 2006, 443, 67-70;
15. (b) Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C.F., III. J Am Chem Soc 2007, 129, 288-289.
16. (a) Vignola, N.; List, B. J Am Chem Soc 2004, 126, 450-451;
17. (b) Kunz, R. K.; MacMillan, D. W. C. J Am Chem Soc 2005, 127, 3240-3241;
18. (c) Marigo, M.; Franzén, J.; Poulsen, T. B.; Zhuang, W.; Jørgensen, K. A. J Am Chem Soc 2005, 127, 6964-6965;
19. (d) Marigo, M.; Schulte, T.; Franzén, J.; Jørgensen, K. A. J Am Chem Soc 2005, 127, 15710-15711;
20. (e) Franzén, J.; Marigo, M.; Fielenbach, D.; Wabnitz, T. C.; Kjaersgaard, A.; Jørgensen, K. A. J Am Chem Soc 2005, 127, 18296-18304;
21. (f) Enders, D.; Hüttl, M. R. M.; Grondal, C.; Raabe, G. Nature 2006, 441, 861-863;
22. (g) Carlone, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Melchiorre, P. Angew Chem Int Ed 2007, 46, 4504-4506;
23. (h) Ibrahem, L; Rios, R.; Vesely, J.; Hammar, P.; Eriksson, L.; Himo, F.; Córdova, A. Angew Chem Int Ed 2007, 46, 4507-4510.
24. (a) Oku, J.; Inoue, S. J Chem Soc Chem Commun 1981, 5, 229-230;
25. (b) Iyer, M. S.; Gigstad, K. M.; Namdev. N. D.; Lipton, M. J Am Chem Soc 1996, 118, 4910-4911;
26. (c) Iyer, M. S.; Gigstad, K. M.; Namdev. N. D.; Lipton, M. Amino Acids 1996, 11, 259-268.
27. (a) Juliá, S.; Masana, J.; Vega, J. C. Angew Chem Int Ed Engl 1980, 19, 929-931;
28. (b) Budt, K. H.; Vatele, J. M.; Kishi, Y. J Am. Chem Soc 1986, 108, 6080-6082;
29. (c) Takagi, R.; Manabe, T.; Shiraki, A.; Yoneshige, A.; Hiraga, Y.; Kojima, S.; Ohkata, K. Bull Chem Soc Jpn 2000, 73, 2115-2121;
30. (d) Takagi, R.; Shiraki, A.; Manabe, T.; Kojima, S.; Ohkata, K. Chem Lett 2000, 4, 366-367;
31. (e) Flood, R. W.; Geller, T. P.; Petty, S. A.; Roberts, S. M.; Skidmore, J.; Volk, M. Org Lett 2001, 3, 683-686;
32. (f) Berkessel, A.; Gasch, N.; Glabitz, K; Koch, C. Org Lett 2001, 3, 3839-3842.
33. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Heidelberg, 1999; Vol.1-3.
34. (a) Burk, M. J.; Feaster, J. E. J Am Chem Soc 1992, 114, 6266-6267;
35. (b) Okuda, J. Verch, S.; Stürmer, R.; Spaniol, T. S. J Organomet Chem. 2000, 605, 55-67;
36. (c) Xial, D.; Zhang, X. Angew Chem Int Ed 2001, 40, 3425-3428;
37. (d) Samec, J. S. M.; Bäckvall, J. E. Chem Eur J 2002, 8, 2955-2961;
38. (e) Blaser, H. U. Adv Synth Catal 2002, 344, 17-31;
39. (f) Cobley, C. J.; Henschke, J. P. Adv Synth Catal 2003, 345, 195-201.
40. (a) Lipshutz, B. H.; Noson, K.; Chrisman, W.; Lower, A. J Am. Chem Soc 2003, 125, 8779-8789;
41. (b) Riant, O.; Mostefai, N.; Courmarcel, J. Synthesis 2004, 18, 2943-2958;
42. (c) Lipshutz, B. H.; Shimizu, H. Angew Chem In. Ed 2004, 43, 2228-2230.
43. (a) Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J Am Chem Soc 1996, 118, 4916-4917;
44. (b) Noyori, R.; Hashiguchi, S. Acc Chem Res 1997, 30, 97-102.
45. (a) Itsuno, S.; Sakurai, Y.; Ito, K.; Hirao, A.; Nakahama, S. Bull Chem Soc Jpn 1987, 60, 395-396;
46. (b) Cho, B. T.; Chun, Y. S. J Chem. Soc Perkin Trans 1990, 1, 3200-3201;
47. (c) Cho, B. T.; Chun, Y. S. Tetrahedron: Asymmetry 1992, 3, 1583-1590.
48. (a) Ingh, S.; Batra, U. K. Indian J Chem 1989, 27, 1-2;
49. (b) Rueping, M.; Sugiono, E.; Azap, C.; Theissmann, T.; Boite, M. Org Lett 2005, 7, 3781-3783;
50. (c) Hoffmann, S.; Seayad, A. M.; List, B. Angew Chem Int Ed 2005, 44, 7424-7427.
51. (a) Kobayashi, S.; Nishio, K. J Org Chem 1994, 59, 6620-6628;
52. (b) Kobayashi, S.; Yasuda, M.; Hachiya, I. Chem Lett 1996, 25, 407-408.
53. (a) Iwasaki, F.; Onomura, O.; Mishima, K.; Maki, T.; Matsumura, Y. Tetrahedron Lett 1999, 40, 7507-7511;
54. (b) Iwasaki, F.; Onomura, O.; Mishima, K.; Kanematsu, T.; Maki, T.; Matsumura, Y. Tetrahedron Lett 2001, 42, 2525-2527.
55. Malkov, A. V.; Mariani, A.; MacDougall, K. N.; Kočovský, P. Org Lett 2004, 6, 2253-2256.
56. (a) Masuda, T.; Sanda, F. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol.3, pp 375-406;
57. (b) Wang, R.; Bélanger-Gariépy, F.; Zargarian, D. Organometallics 1999, 18, 5548-5552;
58. (c) Li, K.; Wei, G.; Darkwa, J.; Pollack, S. K. Macromolecules 2002, 35, 4573-4576;
59. (d) Mayershofer, M. G.; Nuyken, O. J Polym Sci Part A: Polym Chem 2005, 43, 5723-5747;
60. (e) Katsumata, T.; Shiotsuki, M.; Masuda, T. Macromol Chem Phys 2006, 207, 1244-1252.
61. (a) Ciardelli, F.; Lanzillo, S.; Pieroni, O. Macromolecules 1974, 7, 174-179;
62. (b) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390;
63. (c) Yamaguchi, M.; Omata, K.; Hirama, M. Chem Lett 1992, 21, 2261-2262;
64. (d) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem Lett 1993, 22, 2009-2010;
65. (e) Yashima, E.; Huang, S.; Okamoto, Y. J Chem Soc Chem Commun 1994, 15, 1811-1812;
66. (f) Yashima, E.; Huang, S.; Matsushima, T.; Okamoto, Y. Macromolecules 1995, 28, 4184-4193;
67. (g) Nakako, H.; Nomura, R.; Tabata, M.; Masuda, T. Macromolecules 1999, 32, 2861-2864;
68. (h) Nomura, R.; Fukushima, Y.; Nakako, H.; Mauda, T. J Am Chem Soc 2000, 122, 8830-8836.
69. Tabata, M.; Yang, Y.; Yokota, K. Polym J 1990, 22, 1105-1107.
70. Reviews: (a) Yashima, E.; Maeda, K.; Nishimura, T. Chem Eur J 2004, 10, 42-51;
71. (b) Lam, J. W. Y.; Tang, B. Z. Acc Chem Res 2005, 38, 745-754;
72. (c) Aoki, T.; Kaneko, T.; Teraguchi, M. Polymer, 2006, 47, 4867-4892.
73. (a) Gao, G.; Sanda, F.; Masuda, T. Macromolecules 2003, 36, 3932-3937;
74. (b) Gao, G.; Sanda, F.; Masuda, T. Macromolecules 2003, 36, 3938-3943;
75. (c) Sanda, F. Araki, H.; Masuda, T. Macromolecules 2004, 37, 8510-8516;
76. (d) Sanda, F. Terada, K.; Masuda, T. Macromolecules 2005, 38, 8149-8154.
77. (a) Cheuk, K. K. L.; Li, B. S.; Tang, B. Z. In Encyclopedia of Nanoscience and Nanotechnology; Nalwa, H. S., Ed.; American Scientific Publishers: Stevenson Ranch, CA, 2004; Vol.8, pp 703-713;
78. (b) Li, B.; Kang, S.; Cheuk, K. K. L.; Wan, L.; Ling, L.; Bai, C.; Tang, B. Z. Langmuir 2004, 20, 7589-7597;
79. (c) Lai, L. M.; Lam, J. W.Y.; Qin, A.; Dong, Y.; Tang, B. Z. J Phys Chem B 2006,110,11128-11138.
80. (a) Nonokawa, R.; Yashima, E. J Am Chem Soc 2003, 125, 1278-1283;
81. (b) Onouchi, H.; Hasegawa, T. Kashiwagi, D.; Ishiguro, H.; Maeda, K.; Yashima, E. Macromolecules 2005, 38, 8625-8633;
82. (c) Maeda, K.; Tsukui, H.; Matsushita, Y.; Yashima, E. Macromolecules 2007, 40, 7721-7726.
83. (a) Reggelin, M.; Schultz, M.; Holbach, M. Angew Chem Int Ed 2002, 41, 1614-1617;
84. (b) Reggelin, M.; Doerr, S.; Klussmann, M.; Schultz, M.; Holbach, M. Proc Natl Acad Sci USA 2004, 101, 5461-5466;
85. (c) Itsuno, S. Prog Polym Sci 2005, 30, 540-558;
86. (d) Buchmeiser, M. R. Chem Rev 2009, 109, 303-321;
87. (e) Ikegami, S.; Hamamoto, H. Chem Rev 2009, 109, 583-593;
88. (f) Lu, J.; Toy, P. H. Chem Rev 2009, 109, 815-838.
89. (a) Sanda, F. Araki, H.; Masuda, T. Chem Lett 2005, 34, 1642-1643;
90. (b) Maeda, K.; Tanaka, K.; Morino, K.; Yashima, E. Macromolecules 2007, 40, 6783-6785.
91. (a) Schnider, P.; Koch, G.; Pretot, R.; Wang, G.; Bohnen, F. Chem Eur J 1997, 3, 887-892;
92. (b) Samec, J. S. M.; Bäckvall, J. E. Chem Eur J 2002, 8, 2955-2961;
93. (c) Cheemala, M. N.; Knochel, P. Org Lett 2007, 9, 3089-3092.
94. Schrock, R. R.; Osborn, J. A. Inorg Chem 1970, 9, 2339-2343.
95. (a) Dekkers H. P. J. M. In Circular Dichroism: Principles and Applications, 2nd ed.; Berova, N., Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH: Weinheim, 2000; Chapter 7;
96. (b) Fujiki, M. Macromol Rapid Commun 2001, 22, 539-563.
97. (a) Nomura, R.; Tabei, J.; Masuda, T. J Am Chem Soc 2001, 123, 8430-8431;
98. (b) Tabei, J.; Nomura, R.; Masuda, T. Macromolecules 2002, 35, 2955-2961;
99. (c) Tabei, J.; Nomura, R.; Masuda, T. Macromolecules 2002, 35, 5405-5409;
100. (d) Tabei, J.; Nomura, R.; Sanda, F.; Masuda, T. Macromolecules 2003, 36, 8603-8608;
101. (e) Yue, D.; Fujii, T.; Terada, K.; Tabei, J.; Shiotsuki, M.; Sanda, F.; Masuda, T. J Polym Sci Part A: Polym Chem 2007, 45, 1515-1524;
102. (f) Suzuki, Y.; Tabei, J.; Shiotsuki, M.; Inai, Y.; Sanda, F.; Masuda, T. Macromolecules 2008, 41, 1086-1093.
103. (a) Nakako, H.; Nomura, R.; Tabata, M.; Masuda, T Macromolecules 1999, 32, 2861-2864;
104. (b) Nakako, H.; Mayahara, Y.; Nomura, R.; Tabata, M.; Masuda, T. Macromolecules 2000, 33, 3978-3982;
105. (c) Nomura, R.; Fukishima, Y.; Nakako, H.; Masuda, T. J Am Chem Soc 2000, 122, 8830-8836;
106. (d) Nakako, H.; Nomura, R.; Masuda, T. Macromolecules 2001, 34, 1496-1502.
107. (a) Suzuki, Y.; Shiotsuki, M.; Sanda, F.; Masuda, T. Macromolecules 2007, 40, 1864-1867;
108. (b) Suzuki, Y.; Shiotsuki, M.; Sanda, F.; Masuda, T. Chem Asian J 2008, 3, 2075-2081.
109. (a) Sakurai, S.; Okoshi, K.; Kumaki, J.; Yashima, E. J Am Chem Soc 2006, 128, 5650-5651;
110. (b) Sakurai, S.; Okoshi, K.; Kumaki, J.; Yashima, E. Angew Chem Int Ed 2006, 45, 1245-1248.
111. One reviewer suggested that the reversal of the selectivity may be caused by the coordination of two formamides to trichlorosilane in the polymer catalysts. If we could synthesize dimer and trimer catalysts, we could obtain further information on the mechanism, of enantioselectivity by the polymer catalyst opposite to that by the monomer catalyst. Unfortunately, it is very difficult to synthesize the dimer and trimer.