Highly enantioselective oxidative couplings of 2-naphthols catalyzed by chiral bimetallic oxovanadium complexes with either oxygen or air as oxidant

Journal of the American Chemical Society

Volumn 129, Issue 45, 2007, Pages 13927-13938

  Guo, Qi Xiang ^a,e   Wu, Zhi Jun ^c   Luo, Zhi Bin ^b   Liu, Quan Zhong ^b   Ye, Jian Liang ^d   Luo, Shi Wei ^a   Cun, Lin Feng ^b   Gong, Liu Zhu ^a,b  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^b CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c CHENGDU INSTITUTE OF BIOLOGY   (China)

^d XIAMEN UNIVERSITY   (China)

^e UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DENSITY FUNCTIONAL THEORY; ENANTIOSELECTIVITY; KINETICS; OXIDANTS; OXYGEN; VANADIUM COMPOUNDS;

NAPHTHOLS; OXIDATIVE COUPLINGS; OXOVANADIUM;

NAPHTHALENE;

2 NAPHTHOL; AMINO ACID; ISOLEUCINE; LIGAND; METAL COMPLEX; OXIDIZING AGENT; OXYGEN; POLYMER; RADICAL; VANADIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; DENSITY FUNCTIONAL THEORY; DIASTEREOISOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC CHEMISTRY; OXIDATION; QUANTUM MECHANICS; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

AIR; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS; OXIDANTS; OXIDATION-REDUCTION; OXYGEN; STEREOISOMERISM; VANADATES;

EID: 36148990626     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074322f     Document Type: Article

References (95)

1. (a) Kočovský, P.; Vyscočil, Š.; Smŕcina, M. Chem. Rev. 2003, 103, 3213.
2. (b) Chelucci, G.; Thummel, R. P. Chem. Rev. 2002, 102, 3129.
3. (c) Solomon, E. I.; Sundaram, U. M.; Machonkin, T. E. Chem. Rev. 1996, 96, 2563.
4. (a) Noyori, R. Asymmetric Catalysis in the Organic Synthesis; Wiley: New York, 1994.
5. (b) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
6. (c) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis; Springer-Verlag: Berlin, Heidelberg, 1999.
7. (d) Noyori, R. Tetrahedron 1994, 50, 4259.
8. (e) Trost, B. M. Pure Appl. Chem. 1992, 64, 315.
9. (f) Hayashi, T.; Kudo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421.
10. (g) Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021.
11. (h) Kagan, H. B.; Riant, O. Chem. Rev. 1992, 92, 1007.
12. (i) Blaser, H.-U. Chem. Rev. 1992, 92, 935.
13. (j) Rosini, G.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
14. (k) Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
15. (l) Brunel, J. M. Chem. Rev. 2005, 105, 857.
16. For a review, see: (a) Coleman, R. S.; Madaras, M. L. In The Chemical Synthesis of Natural Products; Hale, K. J., Ed; CRC Press: Sheffield, 2000; Chapter 6, pp 144-179.
17. For reviews, see: (a) Pu, L. Chem. Rev. 1998, 98, 2405.
18. (b) Pu, L. Chem. Rev. 2004, 104, 1687.
19. For leading representative original researches, see: (c) Irie, M.; Yorozu, T.; Hayashi, K. J. Am. Chem. Soc. 1978, 100, 2236.
20. (d) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Nature 1995, 374, 345.
21. (e) Akagi, K.; Piao, G.; Kaneko, S.; Sakamaki, K.; Shirakawa, H.; Kyotani, M. Sciences 1998, 282, 1683.
22. (f) Zheng, L.; Urian, R. C.; Liu, Y.; Jen, A. K. Y.; Pu, L. Chem. Mater. 2000, 12, 13.
23. (g) Pugh, V. J.; Hu, Q. S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638.
24. (h) Gong, L. Z.; Hu, Q. S.; Pu, L. J. Org. Chem. 2001, 66, 2358.
25. (i) Lin, J.; Hu, Q. S.; Xu, M. H.; Pu, L. J. Am. Chem. Soc. 2002, 124, 2088.
26. (j) Cui, Y.; Evans, O. R.; Ngo, H. L.; White, P. S.; Lin, W. B. Angew. Chem., Int. Ed. 2002, 41, 1159.
27. (a) Sharma, V. B.; Jain, S. L.; Sain, B. Tetrahedron Lett. 2003, 44, 2655.
28. (b) Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
29. (c) Hwang, D.-R.; Chen, C.-P.; Uang. B.-J. Chem. Commun. 1999, 1207.
30. (d) Yadav, J. S.; Reddy, B. V. S.; Gayathri, K. U.; Prasad, A. R. New J. Chem. 2003, 27, 1684.
31. (e) Umare, P. S.; Tembe, G. L. React. Kinet. Catal. Lett. 2004, 82, 173.
32. (f) Gupta, R.; Mukherjee, R. Tetrahedron Lett. 2000, 41, 7763.
33. (g) Nishino, H.; Satoh, H.; Yamashita, M.; Kurosawa, K. J. Chem. Soc., Perkin Trans. 2 1999, 1919.
34. (h) Ding, K.; Wang, Y.; Zhang, L.; Wu, Y.; Matsuura, T. Tetrahedron 1996, 52, 1005.
35. (i) Dewar, M. J. S.; Nakaya, T. J. Am. Chem. Soc. 1968, 90, 7134.
36. (a) Prasad, M. R.; Kamalakar, G.; Kulkarni, S. J.; Raghavan, K. V. J. Mol. Catal. A: Chem. 2002, 180, 109.
37. (b) Armengol, E.; Corma, A.; García, H.; Primo, J. Eur. J. Org. Chem. 1999, 1915.
38. (c) Kantam, M. L.; Kavita, B.; Figueras, F. Catal. Lett. 1998, 51, 113.
39. (d) Mastrorilli, P.; Muscio, F.; Suranna, G. P.; Nobile, C. F.; Latronico, M. J. Mol. Catal. A: Chem. 2001, 165, 81.
40. (e) Sakamoto, T.; Yonehara, H.; Pac, C. J. Org. Chem. 1997, 62, 3194.
41. (f) Iwai, K.; Yamauchi, T.; Hashimoto, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Lett. 2003, 32, 58.
42. (g) Fujiyama, H.; Kohara, I.; Iwai, K.; Nishiyama, S.; Tsuruya, S.; Masai, M. J. Catal. 1999, 188, 417.
43. (h) Matsushita, M.; Kamata, K.; Yamaguchi, K.; Mizuno, N. J. Am. Chem. Soc. 2005, 127, 6632.
44. For resolution of binaphthols, see: (a) Feringa, B.; Wynberg, H. Bioorg. Chem. 1978, 7, 397.
45. (b) Toda, F.; Tanaka, K. J. Org. Chem. 1988, 53, 3607.
46. (c) Pirkle, W. H.; Schreiner, J. L. J. Org. Chem. 1981, 46, 4988.
47. (d) Hu, Q. S.; Vitharana, D.; Pu, L. Tetrahedron: Asymmetry 1995, 6, 2123.
48. (e) Cai, D.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 7991.
49. Aoyama, H.; Tokunaga, M.; Kiyosu, J.; Iwasawa, T.; Obora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2005, 127, 10474.
50. (a) Toda, F.; Tanaka, K.; Miyamoto, H.; Koshima, H.; Miyahara, I.; Hirotsu, K. J. Chem. Soc., Perkin Trans. 1997, 2, 1877.
51. (b) Delogu, G.; Fabbri, D.; Dettori, M. A.; Forni, A.; Casalone, G. Tetrahedron: Asymmetry 2000, 11, 4417.
52. (a) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.-I.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
53. (b) Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3, 1137.
54. (c) Gao, J.; Reibenspies, J. H.; Martell, A. E. Angew. Chem., Int. Ed. 2003, 42, 6008.
55. (d) Li, X.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500.
56. (a) Habaue, S.; Seko, T.; Okamoto, Y. Macromolecules 2002, 35, 2437.
57. (b) Habaue, S.; Seko, T.; Okamoto, Y. Macromolecules 2003, 36, 2604.
58. (c) Tsubaki, K.; Miura, M.; Morikawa, H.; Tanaka, T.; Kawabata, T.; Furuta, T.; Tanaka, K.; Fuji, K. J. Am. Chem. Soc. 2003, 125, 16200.
59. (d) Xie, X.; Phuan, P.-W.; Kozlowski, M. C. Angew. Chem., Int. Ed. 2003, 42, 2168.
60. Mulrooney, C. A.; Li, X.; DiVirgilio, E. S.; Kozlowski, M. C. J. Am. Chem. Soc. 2003, 125, 6856.
61. Irie, R.; Masutani, K.; Katsuki, T. Synlett 2000, 1433.
62. Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang, B.-J. Chem. Commun. 2001, 980.
63. Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N. B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869.
64. (a) Barhatre, N. B.; Chen, C.-T. Org. Lett. 2002, 4, 2529.
65. (b) Chu, C.-Y.; Uang, B.-J. Tetrahedron: Asymmetry 2003, 14, 53.
66. (a) Tada, M.; Taniike, T.; Kantam, L. M.; Iwasawa, Y. Chem. Commun. 2004, 2542.
67. (b) Tada, M.; Kojima, N.; Izumi, Y.; Taniike, T.; Iwasawa, Y. J. Phys. Chem. B 2005, 109, 9905.
68. Luo, Z.; Liu, Q.; Gong, L.; Cui, X.; Mi, A.; Jiang, Y. Z. Chem. Commun. 2002, 914.
69. Luo, Z. B.; Liu, Q. Z.; Gong, L. Z.; Cui, X.; Mi, A. Q.; Jiang, Y. Z. Angew. Chem., Int. Ed. 2002, 41, 4532.
70. (a) Brunner, H.; Schiessling, H. Bull. Soc. Chim. Belg. 1994, 103, 119.
71. (b) Zhang, H. C.; Huang, W. S.; Pu, L. J. Org. Chem. 2001, 66, 481.
72. (a) Theriot, L. J.; Carlisle, G. O.; Hu, H. J. J. Inorg. Nucl. Chem. 1969, 31, 2841.
73. (b) Frausto da Silva, J. J. R.; Wootton, R.; Gillard, R. D. J. Chem. Soc. A 1970, 3369.
74. Tracey, A. S. Coord. Chem. Rev. 2003, 237, 113.
75. (a) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki, M.; Angelaud, R. Angew. Chem., Int. Ed. 2000, 39, 3532.
76. (b) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Matsukawa, S. Acc. Chem. Res. 2000, 33, 391.
77. (c) Mikami, K.; Yamanaka, M. Chem. Rev. 2003, 103, 3369.
78. (d) Faller, J. W.; Lavoie, A. R.; Parr, J. Chem. Rev. 2003, 103, 3345.
79. (e) Ding, K.; Du, H.; Yuan, Y.; Long, J. Chem. Eur. J. 2004, 10, 2872.
80. Walsh, P. J.; Lurain, A. E.; Balsells, J. Chem. Rev. 2003, 103, 3297.
81. Berova, N., Nakanishi, K., Woody, R. W., Eds. Circular Dichroism: Principles and Applications; Wiley-VCH: New York, 2000.
82. (a) Tada, M.; Kojima, N.; Izumi, Y.; Taniike, T.; Iwasawa, Y. J. Phys. Chem. B 2005, 109, 9905.
83. (b) Pessoa, J. C.; Cavaco, I.; Correia, I.; Duarte, M. T.; Gillard, R. D.; Henriques, R. T.; Higes, F. J.; Madeira, C.; Tomaz, I. Inorg. Chim. Acta 1999, 293, 1.
84. Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
85. Somei, H.; Asano, Y.; Yoshida, T.; Takizawa, S.; Yamataka, H.; Sasai, H. Tetrahedron Lett. 2004, 45, 1841.
86. The oxidation reaction of stoichiometic amounts of homochiral chlorovanadate with (S)-ethyl mandelate under unaerobic conditions has been used for the mechanistic investigation, see: Radosevich, A. T.; Musich, C.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 1090.
87. de la Mora, J. F.; Van Berkel, G. J.; Enke, C. G.; Cole, R. B.; Martinez-Sanchez, M.; Fenn, J. B. J. Mass Spectrom. 2000, 35, 939.
88. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford CT, 2004.
89. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
90. (b) Dunning, T. H.; Hay, P. J. In Modem Theoretical Chemistry; Schaefer, H. F., Ed.; Plenum: New York, 1976; Vol. 3, p 1.
91. (c) Ehlers, A. W.; Bohme, M.; Dapprich, S.; Gobbi, A.; Hollwarth, A.; Jonas, V.; Kohler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111.
92. (d) Hollwarth, A.; Bohme, M.; Dapprich, S.; Ehlers, A. W.; Gobbi, A.; Jonas, V.; Kohler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 237.
93. Rehder, D.; Schulzke, C.; Dau, H.; Meinke, C.; Hanss, J.; Epple, M. J. Inorg. Biochem. 2000, 80, 115.
94. Liu, Q.-Z.; Xie, N.-S.; Luo, Z.-B.; Cui, X.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. J. Org. Chem. 2003, 68, 7921-7924.
95. Yuan, W.-C.; Cun, L.-F.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z. Tetrahedron Lett. 2005, 46, 509.