The development of scalemic multidentate niobium complexes as catalysts for the highly stereoselective ring opening of meso-epoxides and meso-aziridines

Journal of the American Chemical Society

Volumn 129, Issue 26, 2007, Pages 8103-8111

  Arai, Kenzo ^a   Lucarini, Simone ^a   Salter, Matthew M ^a   Ohta, Kentaro ^a   Yamashita, Yasuhiro ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSTS; ENANTIOSELECTIVITY; NUCLEOPHILES; RING OPENING POLYMERIZATION; STEREOSELECTIVITY;

CHEMICAL SELECTIVITY; EPOXIDES; LEWIS ACID SYSTEM; MESO-EPOXIDES;

NIOBIUM COMPOUNDS;

ALKENE; ANILINE; AZIRIDINE; EPOXIDE; LEWIS ACID; METAL COMPLEX; NIOBIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY;

CATALYSIS; MACROMOLECULAR SUBSTANCES; MOLECULAR STRUCTURE; NIOBIUM;

EID: 34447117685     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0708666     Document Type: Article

References (132)

1. For reviews see (a) Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 2, Chapter 1.
2. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Heidelberg, Germany, 1999; Vol. 3, p 998.
3. For reviews of Lewis acid catalyzed asymmetric reactions see (a) Bach, T. Angew. Chem., Int. Ed. 1994, 33, 417.
4. (b) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
5. (c) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137.
6. (d) Mahrwald, R. Chem. Rev. 1999, 99, 1095.
7. (e) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
8. (f) Dilman, A. D.; Ioffe, S. L. Chem. Rev. 2003, 103, 733.
9. (g) Shibasaki, M.; Matsunaga, S. J. Organomet. Chem. 2006, 691, 2089.
10. (h) Kobayashi, S.; Ogawa, C. Chem. Eur. J. 2006, 5954.
11. For recent monographs on the chemistry of expoxides and aziridines see (a) Rao, A. S. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 7, p 357.
12. (b) Jacobsen, E. N.; Wu, M. H. Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Germany, 1999; Vol. III, Chapter 35.
13. (c) McCoull, W.; Davis, F. A. Synthesis 2000, 1347.
14. (d) Sweeny, J. B. Chem. Soc. Rev. 2002, 31, 247.
15. (e) Pineschi, M. Eur. J. Org. Chem. 2006, 4979.
16. (a) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433.
17. (b) Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1994, 2597.
18. (c) Hou, X. -L.; Wu, J.; Dai, L. -J.; Tang, M.-H. Tetrahedron: Asymmetry 1998, 9, 1747.
19. (d) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 287.
20. (e) Sagawa, S.; Abe, H.; Hase, Y.; Inabe, T. J. Org. Chem. 1999, 64, 4962.
21. (a) Das, U.; Crousse, B.; Kesavan, V.; Bonnet-Dolpon, D.; Bégué, J. P. J. Org. Chem. 2000, 65, 6749.
22. (b) Chandrasekhar, S.; Ramachandar, T.; Jaya Prakesh, S. Synthesis 2000, 1817.
23. (c) Rajendder Reddy, L.; Arjun Reddy, M.; Bhanumanti, N.; Rama Rao, K. New J. Chem. 2001, 25, 221.
24. (d) Rajendder Reddy, L.; Arjun Reddy, M.; Bhanumanti, N.; Rama Rao, K. Synthesis 2001, 831.
25. (e) Raghavendra Swamy, N.; Kondaji, G.; Nagaiah, K. Synth. Commun. 2002, 32, 2307.
26. (f) Ollevier, T.; Lavie-Compin, G. Tetrahedron Lett. 2002, 43, 7891.
27. (g) Cossy, J.; Bellosta, V.; Hamoir, C.; Desmurs, J. R. Tetrahedron Lett. 2002, 43, 7083.
28. (h) Sekine, A.; Oshima, T.; Shibasaki, M. Tetrahedron 2002, 58, 75.
29. (i) Durán Pachón, L.; Gamez, P.; van Brussel, J. J. M.; Reedijk, J. Tetrahedron Lett. 2003, 44, 6025.
30. (j) Chakraborti, A. K.; Kondaskar, A. Tetrahedron Lett. 2003, 44, 8315.
31. (k) Zhao, P. Q.; Xu, L. W.; Xia, C. G. Synlett 2004, 846.
32. (l) Ollevier, T.; Lavie-Compin, G. Tetrahedron Lett. 2004, 45, 49.
33. (m) Placzek, A. T.; Donelson, J. L.; Trivedi, R.; Gibbs, R. A.; De, S. K. Tetrahedron Lett. 2005, 46, 9029.
34. (n) Kamal, A.; Ramu, R.; Azhar, M. A.; Khanna, G. B. R. Tetrahedron Lett. 2005, 46, 2675.
35. (o) Wu, J.; Xia, H. -G. Green Chem. 2005, 7, 708.
36. (a) Das, B.; Krishnaiah, M.; Venkateswarlu, K. Tetrahedron Lett. 2006, 47, 6027.
37. (b) Huang, J.; O'Brien, P. Synthesis 2006, 425.
38. (c) Bonollo, S.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2006, 8, 960.
39. (d) Schneider, C. Synthesis 2006, 3919.
40. (t) Torregrosa, R.; Pastor, I. M.; Yus, M. Tetrahedron 2006, 63, 469.
41. (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1668.
42. (b) Shimizu, K. D.; Cole, B. M.; Krueger, C. A.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. Angew.Chem., Int. Ed. Engl. 1997, 36, 1704.
43. (c) Schaus, S. E.; Jacobsen, E. N. Org. Lett. 2000, 2, 1001.
44. (d) Yamasaki, S.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 1256.
45. (e) Zhu, C.; Yuan, F.; Gu, W.; Pan, Y. Chem. Commun. 2003, 692.
46. (f) Pakulski, Z.; Pietrusiewiscz, K. M. Tetrahedron: Asymmetry 2004, 15, 41.
47. Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783.
48. Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897.
49. (b) Leighton, J. L.; Jacobsen, E. N. J. Org. Chem. 1996, 61, 389.
50. (a) Iida, T.; Yamamoto, N.; Matsunaga, S.; Woo, H. -G.; Shibasaki, M. Angew. Chem., Int. Ed. 1998, 37, 2223.
51. (b) 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. (c) Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 2687.
53. (a) Hou, X. -L.; Wu, J.; Dai, L. -X.; Xia, L. -J.; Tang M. -H. Tetrahedron: Assymmetry 1998, 9, 1747.
54. (b) Sekine, A.; Ohshima, T.; Shibasaki, M. Tetrahedron 2002, 58, 75.
55. (c) Schneider, C.; Sreekanth, A. R.; Mai, E. Angew. Chem., Int. Ed. 2004, 43, 5691.
56. (d) Carrée, F.; Gil, R.; Collin, J. Tetrahedron Lett. 2004, 45, 7749.
57. (e) Carrée, F.; Gil, R.; Collin, J. Org. Lett. 2005, 7, 1023.
58. (f) Kureshy, R. I.; Singh, S.; Khan, N. H.; Abdi, S. H. R.; Suresh, E.; Jasra, R. V. Eur. J. Org. Chem. 2006, 1303.
59. (g) Kureshy, R. I.; Singh, S.; Khan, N. H.; Abdi, S. H. R.; Agrawal, S.; Mayani, V. J.; Jasra, R. V. Tetrahedron Lett. 2006, 47, 5277.
60. (h) Mai, E. Schneider, C. Chem. Eur. J. 2007, 2729.
61. (a) Alexakis, A.; Vranken, E.; Mangeney, P. Synlett 1998, 11165.
62. (b) Vranken, E.; Alexakis, A.; Mangeney, P. Eur. J. Org. Chem. 2005, 1354.
63. Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
64. Muller, P.; Nury, P. Org. Lett. 1999, 1, 439.
65. (a) Li, Z.; Fernandez, M.; Jacobsen, E. N. Org. Lett. 1999, 1, 1611.
66. (b) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312.
67. (a) Ishitani, H.; Yamashita, Y.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 5403.
68. (b) Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292.
69. (c) Kobayashi, S.; Saito, S.; Ueno, M.; Yamashita, Y. Chem. Commun. 2003, 2016.
70. (d) Kobayashi, J.; Nakamura, M.; Mori, Y.; Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 9192.
71. (a) Kobayashi, S.; Komiyama, S.; Ishitani, H. Angew. Chem., Int. Ed. 1998, 37, 979.
72. (b) Kobayashi, S.; Kusakabe, K. -I.; Komiyama, S.; Ishitani, H. J. Org. Chem. 1999, 64, 4220.
73. (c) Kobayashi, S.; Kusakabe, K. -I.; Ishitani, H. Org. Lett. 2000, 2, 1225.
74. (d) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. Org. Lett. 2002, 4, 1221.
75. (e) Kobayashi, S.; Shimizu, H.; Yamashita, Y.; Ishitani, H.; Kobayashi, J. J. Am. Chem. Soc. 2002, 124, 13678.
76. (f) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3793.
77. (g) Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 11279.
78. (h) Kobayashi, S.; Ueno, M.; Saito, S.; Mizuki, Y.; Ishitani, H.; Yamashita, Y. Proc. Natl. Acad. Sci. 2004, 101, 5476.
79. (i) Yamashita, Y.; Mizuki, Y.; Kobayashi, S. Tetrahedron Lett. 2005, 46, 1803.
80. (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
81. (b) Ishitani, H.; Komiyama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 1998, 37, 3186.
82. (c) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
83. (d) Kobayashi, S.; Hasegawa, Y.; Ishitani, H. Chem. Lett. 1998, 1131.
84. (e) Ishitani, H.; Kitazawa, T.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 2161.
85. (f) Ishitani, H.; Ueno, M. Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180.
86. (g) Kobayashi, S.; Kobayashi, J.; Ishitani, H.; Ueno, M. Chem. Eur. J. 2002, 8, 4185.
87. Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762.
88. Gastner, T.; Ishitani, H.; Akiyama, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2001, 40, 1896.
89. (a) Kobayashi, S.; Shimizu, H.; Yamashita, Y.; Ishitani, H.; Kobayashi, J. J. Am. Chem. Soc. 2002, 124, 13678.
90. (b) Yamashita, Y.; Kobayashi, S. J. Am. Chem. Soc. 2004, 126, 11279.
91. (a) Azoulay, S.; Manabe, K.; Kobayashi, S. Org. Lett. 2005, 7, 4593.
92. (b) Ogawa, C.; Azoulay, S.; Kobayashi, S. Heterocycles 2005, 66, 201.
93. (c) Boudou, M.; Ogawa, C.; Kobayashi, S. Adv. Synth. Catal. 2006, 348, 2585.
94. For a preliminary description of our early investigations see Arai, K.; Salter, M. M.; Yamashita, Y.; Kobayashi, S. Angew. Chem., Int. Ed. 2007, 46, 955.
95. 5 (Ni→Nb) has been reported: Constantino, M. G.; Lacerda, V., Jr.; Aragão, V. Molecules 2001, 6, 770.
96. For some other applications of niobium salts in synthesis see (a) Suzuki, K.; Hashimoto, T.; Maeta, H.; Matsumoto, T. Synlett 1992, 125.
97. (b) Hashimoto, T.; Maeta, H.; Matsumoto, T.; Morooka, M.; Ohba, S.; Suzuki, K. Synlett 1992, 340.
98. (c) Colletti, S. L.; Halterman, R. L. J. Organomet. Chem. 1993, 455, 99.
99. (d) Maeta, H.; Nagasawa, T.; Handa, Y.; Takei, T.; Osamura, Y.; Suzuki, K. Tetrahedron Lett. 1995, 36, 899.
100. (e) Howarth, J.; Gillespie, K. Tetrahedron Lett. 1996, 37, 6011.
101. (f) Yamamoto, M.; Nakazawa, M.; Kishikawa, K.; Kohmoto, S. Chem. Commun. 1996, 2353.
102. (g) Howarth, J.; Gillespie, K. Molecules 2000, 5, 993.
103. (h) Andrade, C. K. Z.; Azevedo, N. R. Tetrahedron Lett. 2001, 42, 6473.
104. (i) Andrade, C. K. Z.; Oliveira, G. R. Tetrahedron Lett. 2002, 43, 1935.
105. (j) Miyazaki, T.; Katsuki, T. Synthesis 2003, 1046.
106. (k) Arai, S.; Sudo, Y.; Nishida, A. Synlett 2004, 1104.
107. (l) Arai, S.; Takita, S.; Nishida, A. Eur. J. Org. Chem. 2005, 5262.
108. (m) Yadav, J. S.; Subba Reddy, B. V.; Eeshwaraiah, B.; Reddy, P. N. Tetrahedron 2005, 61, 875.
109. (n) Arai, S.; Sudo, Y.; Nishida, A. Tetrahedron 2005, 61, 4639.
110. (o) Hotha, S.; Tripathi, A. Tetrahedron Lett. 2005, 46, 4555.
111. (p) Sudo, Y.; Arai, S.; Nishida, A. Eur. J. Org. Chem. 2006, 752.
112. (q) Yadav, Y. S.; Narsaiah, A. V.; Basak, A. K.; Goud, P. R.; Sreenu, D.; Nagaiah, K. J. Mol. Catal. A: Chem. 2006, 255, 78.
113. Kobayashi, S.; Arai, K.; Shimizu, H.; Ihori, Y.; Ishitani, H.; Yamashita, Y. Angew. Chem., Int. Ed. 2005, 44, 761.
114. For examples of racemic ring-opening reactions of aziridines see (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
115. (b) Meguro, M.; Asao, N.; Yamamoto, Y. Tetrahedron Lett. 1994, 35, 7395.
116. (c) Leung, W. -H.; Yu, M.-T.; Wu, M.-C.; Yeung, L.-L. Tetrahedron Lett. 1996, 37, 891.
117. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693.
118. (e) Lucet, D.; Le Gall, T.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
119. (f) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 2537.
120. (g) Chandrasekhar, M.; Sekhar, G.; Singh, V. K. Tetrahedron Lett. 2000, 41, 10079.
121. (h) Wu, J.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 2000, 65, 1344.
122. (i) Sweeney, J. B. Chem. Soc. Rev. 2002, 31, 247.
123. (j) Cossy, J.; Bellosta, V.; Alauze, V.; Desmurs, J. -R. Synthesis 2002, 2211.
124. (k) Yadav, J. S.; Subba Reddy, B. V.; Vishweshwar Rao, K.; Saritha Raj, K.; Prasad, A. R. Synthesis 2002, 1061.
125. (l) Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2003, 68, 5160.
126. (m) Bisai, A.; Pandey, G.; Pandey, M. K.; Singh, V. K. Tetrahedron Lett. 2003, 44, 5839.
127. (n) Yadav, J. S.; Subba Reddy, B. V.; Baishya, G.; Venkatram Reddy, P.; Harshavardhan, S. J. Synthesis 2004, 1854.
128. (o) Fan, R.-H.; Zhou, Y.-G.; Zhang, W.-X.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 2004, 69, 335.
129. (p) Yadav, J. S.; Subba Reddy, B. V.; Jyothirmai, B.; Murty, M. S. R. Tetrahedron Lett. 2005, 46, 6385.
130. (q) Minakata, S.; Okada, Y.; Oderaotoshi, Y.; Mokatsu, M. Org. Lett. 2005, 7, 3509.
131. (r) Wu, J.; Sun, X.; Ye, S.; Sun, W. Tetrahedron Lett. 2006, 47, 4813.
132. Aoyama, H.; Tokunaga, M.; Kiyosu, J.; Iwasawa, T.; Obora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2005, 127, 10474.