Catalytic asymmetric ring-opening reaction of meso-epoxides with aryl selenols and thiols catalyzed by a heterobimetallic gallium-titanium-salen complex

Advanced Synthesis and Catalysis

Volumn 351, Issue 6, 2009, Pages 920-930

  Sun, Jiangtao ^a   Yang, Minghua ^a   Yuan, Fang ^a   Jia, Xuefeng ^a   Yang, Xia ^a   Pan, Yi ^a   Zhu, Chengjian ^a,b  

^a NANJING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Asymmetric catalysis; Catalyst design; Ep oxides; Gallium; Synthetic methods

Indexed keywords

EID: 65349127176     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800767     Document Type: Article

References (99)

1. a) M. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290;
2. Angew. Chem. Int. Ed. Engl. 1997, 36, 1236;
3. b) J. A. Ma, D. Cahard, Angew. Chem. 2004, 116, 4666;
4. Angew. Chem. Int. Ed. 2004, 43, 4566;
5. c) G. M. Sammis, H. Danjo, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 9928;
6. d) K. Ohno, Y. Kataoka, K. Mashima, Org. Lett. 2004, 6, 4695;
7. e) Z. Luo, Q. Liu, L. Gong, X. Cui, A. Mi, Y. Jiang, Angew. Chem. 2002, 114, 4714;
8. Angew. Chem. Int. Ed. 2002, 41, 4532.
9. a) H. Sasai, T. Arai, Y. Satow, K. N. Houk, M. Shibasaki, J. Am. Chem. Soc. 1995, 117, 6194;
10. b) T. Arai, H. Sasai, K, Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996, 108, 103;
11. Angew. Chem. Int. Ed. Engl. 1996, 35,104;
12. c) M. A. Y. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942;
13. Angew. Chem. Int. Ed. Engl. 1997, 36, 1871;
14. d) T. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383;
15. Angew. Chem. Int. Ed. 1998, 37, 2223;
16. e) S. Matsunaga, J. Das, J. Roels, E. M. Vogl, N, Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252;
17. f) J. Tian, N. Ya-magiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2002, 114, 3788;
18. Angew. Chem. Int. Ed. 2002, 41, 3636;
19. g) N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2004, 116, 4593;
20. Angew. Chem, Int. Ed. 2004, 43, 4493.
21. a) Y. Horiuchi, V. Gnanadesikan, T. Ohshima, H. Masu, K. Katagiri, Y. Sei, K. Yamaguchi, M. Shibasaki, Chem. Ear. J. 2005, 11, 5195;
22. b) S. Tosaki, K. Hara, V. Gnanadesikan, H. Morimoto, S. Harada, M. Sugita, N. Yamagiwa, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 11776;
23. c) Z. Chen, H. Morimoto, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 2170;
24. d) T. Sone, A. Yamaguchi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 10078;
25. e) G. Lu, H. Morimoto, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 6953;
26. Angew. Chem. Int. Ed. 2008, 47, 6847;
27. f) Y. Tanaka, M. Kanai, M. Shibasaki, Synlett 2008, 2295;
28. g) M. Shibasaki, S. Matsunaga, N. Kumagai, Synlett 2008,1583.
29. a) E. E DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 1641;
30. b) Y.N. Belokon, A. J. Blacker, L. A. Clutter-buck, M. North, Org. Lett. 2003, 5, 4505;
31. c) C. Mazet, E. N. Jacobsen, Angew. Chem. 2008, 120, 1786;
32. Angew. Chem. Int. Ed. 2008, 47,1762.
33. a) S. Handa, V. Gnanadesikan, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 4900;
34. b) S. Handa, K. Nagawa, Y. Sohtome, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 3274;
35. Angew. Chem. Int. Ed. 2008, 47, 3230.
36. a) T. Katsuki, Adv. Synth. Catal. 2002, 344, 131;
37. b) T. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691;
38. c) P. G. Cozzi, Chem. Soc. Rev. 2004, 55, 410;
39. d) T. Katsuki, Chem. Soc. Rev. 2004, 33, 437.
40. a) G. M. Sammis, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 4442;
41. b) S. X. Wang, M. X. Wang, D. X. Wang, J. Zhu, Angew. Chem. 2008, 120, 394;
42. Angew. Chem. Int. Ed. 2008, 47, 388;
43. c) T. Yue, M. X. Wang, D. X. Wang, J. Zhu, Angew. Chem. 2008, 120, 9596;
44. Angew. Chem. Int. Ed. 2008, 47, 9454.
45. For review see: D. A. Atwood, M. J. Harvey, Chem. Rev. 2001, 101, 37.
46. M. S. Hill, P. Wei, D. A. Atwood, Polyhedron 1998, 17, 811.
47. For reviews, see: a) E. N. Jacobsen, Ace. Chem. Res. 2000, 33, 421;
48. b) C. Schneider, Synthesis 2006, 3919;
49. c) I. M. Pastor, M. Yus, Curr. Org. Chem. 2005, 9,1.
50. Selected examples for the ring-opening reaction with different nucleophiles: a) X. L. Hou, J. Wu, L. X. Dai, L. J. Xia, M. H. Tang, Tetrahedron: Asymmetry 1998, 9, 1747;
51. b) S. Sagawa, H. Abe, Y. Hase, T. Inaba, J. Org. Chem. 1999, 64, 4962;
52. c) A. Sekine, T. Ohshima, M. Shibasaki, Tetrahedron 2002, 58, 75;
53. d) F. Carree, R. Gil, J. Collin, Org. Lett. 2005, 7, 1023;
54. e) R. I. Kureshy, S. Singh, N. H. Khan, S. H. R. Abdi, E. Suresh, R. V. Jasra, Eur. J. Org. Chem. 2006, 1303;
55. f) C. Schneider, A. R. Sreekanth, E, Mai, Angew. Chem. 2004, 116, 5809;
56. Angew. Chem. Int. Ed. 2004, 43, 5691;
57. g) E. Mai, C. Schneider, Synlett 2007, 2136;
58. h) E. Mai, C. Schneider, Chem. Eur. J. 2007, 13, 2729;
59. i) B. Gao, Y. Wen, Z. Yang, X, Huang, X. Liu, X. Feng, Adv. Synth. Catal. 2008, 350, 385;
60. j) S. Azoulay, K. Manabe, S. Kobayashi, Org. Lett. 2005, 7, 4593;
61. k) K. Arai, M. M. Salter, Y. Yamashita, S. Kobayashi, Angew. Chem. 2007, 119, 973;
62. Angew. Chem. Int. Ed. 2007, 46, 955;
63. l) K. Arai, S. Lu-carini, M. M. Salter, K. Ohta, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2007, 129, 8103;
64. m) J. Sun, Z. Dai, M. Yang, X. Pan, C. Zhu, Synthesis 2008, 2100;
65. n) B, Simona, F. Francesco, P. Ferdinando, V. Luigi, Synlett 2008, 1574;
66. o) S. E, Schaus, E. N. Jacobsen, Org. Lett. 2000, 2, 1001;
67. p) B. Tao, M. M, C. Lo, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 353;
68. q) Z. B. Luo, X. L. Hou, L. X. Dai, Tetrahedron: Asymmetry 2007, 18, 443;
69. r) A. Tschop, A. Marx, A, R. Sreekanth, C. Schneider, Eur. J. Org. Chem. 2007, 2318;
70. s) H.; Bao, J. Zhou, Z. Wang, Y. Guo, T. You, K. Ding, J. Am. Chem. Soc. 2008, 130, 10116;
71. t) B. Saha, M. H. Lin, T. V. RajanBa-bu, J. Org. Chem. 2007, 72, 8648.
72. a) H. Yamashita, T. Mukaiyama, Chem. Lett. 1985, 1643;
73. b) T. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783;
74. c) J. Wu, X. Hou, L. Dai, L. Xia, M. Tang, Tetrahedron: Asymmetry 1998, 9, 3431;
75. d) M, Boudou, C, Ogawa, S. Kobayashi, Adv. Synth. Catal. 2006, 348, 2585;
76. e) C. Ogawa, N. Wang, S. Kobayashi, Chem. Lett. 2007, 36, 34;
77. f) M. V. Nandaku-mar, A. Tschop, H. Krautscheid, C. Schneider, Chem. Commun. 2007, 2756;
78. g) M. H. Wu, E. N. Jacobsen, J. Org. Chem. 1998, 63, 5252;
79. h) Y. J, Chen, C. Chen, Tetrahedron: Asymmetry 2007, 18, 1313;
80. i) J. Sun, F. Yuan, M. Yang, Y. Pan, C. Zhu, Tetrahedron Lett. 2009, 50, 548;
81. j) Z. Zhou, Z. Li, Q. Wang, B. Liu, K. Li, G. Zhao, Q. Zhou, C. Tang, J. Organomet. Chem. 2006, 691, 5790.
82. a) M. Yang, C. Zhu, F. Yuan, Y. Huang, Y. Pan, Org. Lett. 2005, 7, 1927;
83. b) A. Tschop, M. V. Nandakumar, O. Pavlyuk, C. Schneider, Tetrahedron Lett. 2008, 49, 1030.
84. J.F. Larrow, E. N. Jacobsen, Y. Gao, Y. Hong, X. Nie, C. M. Zepp, J. Org. Chem. 1994, 59,1939.
85. a) E. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 3053;
86. b) E. F. DiMauro, M. C. Kozlowski, J. Am. Chem. Soc. 2002, 124,12668.
87. C. Zhu, M. Yang, J. Sun, Y. Zhu, Y. Pan, Synlett 2004, 468.
88. a) J. Sun, C. Zhu, Z. Dai, M. Yang, Y. Pan, H. Hu, J. Org. Chem. 2004, 69, 8500;
89. b) H. Yang, H. Wang, C. Zhu, J. Org. Chem. 2007, 72, 10029;
90. c) Y. Sawada, K. Matsumoto, S. Kondo, H. Watanabe, T. Ozawa, K. Suzuki, B. Saito, T. Katsuki, Angew. Chem. 2006, 118, 3558;
91. Angew. Chem. Int. Ed. 2006, 45, 3478;
92. d) H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 8940;
93. e) Y. Xiong, F. Wang, X. Huang, Y. Wen, X. Feng, Chem. Eur. J. 2007, 13, 829;
94. f) H. Egami, T. Katsuki, Synlett 2008, 1543;
95. g) K. P. Bryliakov, E. P. Talsi, Eur. J. Org. Chem. 2008, 3369.
96. Y. Huang, F. Yang, C. Zhu, J. Am. Chem. Soc. 2005, 127, 16386.
97. J. Gao, J. H. Reibenspies, A. E. Martell, Angew. Chem. 2003, 115, 6190;
98. Angew. Chem, Int. Ed. 2003, 42, 6008.
99. R. G. Pearson, J. Am. Chem. Soc. 1963, 85, 3533.