In situ evaluation of kinetic resolution catalysts for nitroaldol by rationally designed fluorescence probe

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 3616-3625

  Matsumoto, Takuya ^a,d   Urano, Yasuteru ^a   Takahashi, Yoshinori ^b,d   Mori, Yusuke ^b,c,d   Terai, Takuya ^a,d   Nagano, Tetsuo ^a,d  

^a UNIVERSITY OF TOKYO   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c 313 Photonics Center Building   (Japan)

^d JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC CATALYSTS; CHEMICAL CATALYST; FLUORESCENCE INTENSITIES; FLUORESCENCE PROBES; HYDROXYL GROUPS; IN-SITU; KINETIC RESOLUTION; NITROALDOL; NITROOLEFINS; ORGANIC CHEMISTRY; REACTION MIXTURE; REACTION YIELDS; SCREENING SYSTEM; SUPERIOR CATALYSTS;

ACYLATION; CATALYSTS; ENANTIOSELECTIVITY; KINETICS; OLEFINS; PROBES;

FLUORESCENCE;

ALKENE DERIVATIVE; BENZOTETRAMISOLE; FLUORESCENT DYE; FUNCTIONAL GROUP; HYDROXYL GROUP; NITROALDOL; NITROOLEFIN; TETRAMISOLE; UNCLASSIFIED DRUG;

ACYLATION; ALDOL REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; CONTROLLED STUDY; ELIMINATION REACTION; ENANTIOMER; ENANTIOSELECTIVITY; FLUORESCENCE ANALYSIS; KINETICS; PURIFICATION; SYNTHESIS;

BORON COMPOUNDS; CATALYSIS; DRUG DESIGN; FLUORESCENT DYES; HETEROCYCLIC COMPOUNDS, 3-RING; KINETICS; NITRO COMPOUNDS; STEREOISOMERISM;

EID: 79956161717     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1020344     Document Type: Article

References (62)

1. Reetz, M. T. Angew. Chem., Int. Ed. 2002, 41, 1335-1338
2. Reetz, M. T.; Kuhling, K. M.; Deege, A.; Hinrichs, H.; Belder, D. Angew. Chem., Int. Ed. 2000, 39, 3891-3893
3. Wolf, C.; Hawes, P. A. J. Org. Chem. 2002, 67, 2727-2729
4. Reetz, M. T.; Becker, M. H.; Klein, H. W.; Stockigt, D. Angew. Chem., Int. Ed. 1999, 38, 1758-1761
5. Diaz, D. D.; Yao, S. L.; Finn, M. G. Tetrahedron Lett. 2001, 42, 2617-2619
6. Evans, M. A.; Morken, J. P. J. Am. Chem. Soc. 2002, 124, 9020-9021
7. Nishida, Y.; Kim, J. H.; Ohrui, H.; Meguro, H. J. Am. Chem. Soc. 1997, 119, 1484-1485
8. Hattori, T.; Minato, Y.; Yao, S. L.; Finn, M. G.; Miyano, S. Tetrahedron Lett. 2001, 42, 8015-8018
9. Ding, K. L.; Ishii, A.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 497-501
10. Arai, T.; Watanabe, M.; Fujiwara, A.; Yokoyama, N.; Yanagisawa, A. Angew. Chem., Int. Ed. 2006, 45, 5978-5981
11. Taylor, S. J.; Morken, J. P. Science 1998, 280, 267-270
12. Evans, C. A.; Miller, S. J. Curr. Opin. Chem. Biol. 2002, 6, 333-338
13. Korbel, G. A.; Lalic, G.; Shair, M. D. J. Am. Chem. Soc. 2001, 123, 361-362
14. Tanaka, F.; Thayumanavan, R.; Mase, N.; Barbas, C. F. Tetrahedron Lett. 2004, 45, 325-328
15. Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123-2132
16. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 4306-4307
17. Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2004, 126, 9152-9153
18. Stauffer, S. R.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 6977-6985
19. Harris, R. F.; Nation, A. J.; Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2000, 122, 11270-11271
20. Guo, H. M.; Tanaka, F. J. Org. Chem. 2009, 74, 2417-2424
21. Tanaka, F.; Thayumanavan, R.; Barbas, C. F. J. Am. Chem. Soc. 2003, 125, 8523-8528
22. Tanaka, F.; Mase, N.; Barbas, C. F. J. Am. Chem. Soc. 2004, 126, 3692-3693
23. Barder, T. E.; Buchwald, S. L. Org. Lett. 2007, 9, 137-139
24. Pu, L. Chem. Rev. 2004, 104, 1687-1716
25. Han, F.; Chi, L. N.; Liang, X. F.; Ji, S. M.; Liu, S. S.; Zhou, F. K.; Wu, Y. B.; Han, K. L.; Zhao, J. Z.; James, T. D. J. Org. Chem. 2009, 74, 1333-1336
26. Leung, D.; Folmer-Andersen, J. F.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12318-12327
27. Leung, D.; Anslyn, E. V. J. Am. Chem. Soc. 2008, 130, 12328-12333
28. Li, Z. B.; Lin, J.; Pu, L. Angew. Chem., Int. Ed. 2005, 44, 1690-1693
29. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496-6502
30. Tosaki, S. Y.; Hara, K.; Gnanadesikan, V.; Morimoto, H.; Harada, S.; Sugita, M.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 11776-11777
31. Handa, S.; Nagawa, K.; Sohtome, Y.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2008, 47, 3230-3233
32. Hara, K.; Tosaki, S. Y.; Gnanadesikan, V.; Morimoto, H.; Harada, S.; Sugita, M.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Tetrahedron 2009, 65, 5030-5036
33. Sohtome, Y.; Kato, Y.; Handa, S.; Aoyama, N.; Nagawa, K.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2008, 10, 2231-2234
34. Nitabaru, T.; Nojiri, A.; Kobayashi, M.; Kumagai, N.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 13860-13869
35. Shibasaki, M.; Matsunaga, S.; Kumagai, N. Synlett 2008, 1583-1602
36. Luzzio, F. A. Tetrahedron 2001, 57, 915-945
37. Palomo, C.; Oiarbide, M.; Laso, A. Eur. J. Org. Chem. 2007, 2561-2574
38. Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891-4932
39. Goud, T. V.; Tutar, A.; Biellmann, J. F. Tetrahedron 2006, 62, 5084-5091
40. Yogo, T.; Urano, Y.; Ishitsuka, Y.; Maniwa, F.; Nagano, T. J. Am. Chem. Soc. 2005, 127, 12162-12163
41. Ueno, T.; Urano, Y.; Setsukinai, K.; Takakusa, H.; Kojima, H.; Kikuchi, K.; Ohkubo, K.; Fukuzumi, S.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 14079-14085
42. Gabe, Y.; Urano, Y.; Kikuchi, K.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 3357-3367
43. Kamiya, M.; Urano, Y.; Ebata, N.; Yamamoto, M.; Kosuge, J.; Nagano, T. Angew. Chem.-Int. Edit. 2005, 44, 5439-5441
44. Sunahara, H.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2007, 129, 5597-5604
45. Mineno, T.; Ueno, T.; Urano, Y.; Kojima, H.; Nagano, T. Org. Lett. 2006, 8, 5963-5966
46. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T. Tetrahedron Lett. 1998, 39, 5077-5080
47. Adachi, H.; Takano, K.; Yoshimura, M.; Mori, Y.; Sasaki, T. Jpn. J. Appl. Phys. 2003, 42, L314-L315
48. Adachi, H.; Matsumura, H.; Niino, A.; Takano, K.; Kinoshita, T.; Warizaya, M.; Inoue, T.; Mori, Y.; Sasaki, T. Jpn. J. Appl. Phys. 2004, 43, L522-L525
49. France, S.; Guerin, D. J.; Miller, S. J.; Lectka, T. Chem. Rev. 2003, 103, 2985-3012
50. Ishihara, K.; Kosugi, Y.; Akakura, M. J. Am. Chem. Soc. 2004, 126, 12212-12213
51. Shiina, I.; Nakata, K. Tetrahedron Lett. 2007, 48, 8314-8317
52. Shiina, I.; Nakata, K.; Onda, Y. S. Eur. J. Org. Chem. 2008, 5887-5890
53. Xu, Q.; Zhou, H.; Geng, X. H.; Chen, P. R. Tetrahedron 2009, 65, 2232-2238
54. Birman, V. B.; Li, X. M. Org. Lett. 2006, 8, 1351-1354
55. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294-7299
56. Lu, Y.; Zhao, X.; Chen, Z. N. Tetrahedron: Asymmetry 1995, 6, 1093-1096
57. Sprout, C. M.; Seto, C. T. Org. Lett. 2005, 7, 5099-5102
58. Hamberg, A.; Lundgren, S.; Penhoat, M.; Moberg, C.; Hult, K. J. Am. Chem. Soc. 2006, 128, 2234-2235
59. Onaran, M. B.; Seto, C. T. J. Org. Chem. 2003, 68, 8136-8141
60. Taran, F.; Gauchet, C.; Mohar, B.; Meunier, S.; Valleix, A.; Renard, P. Y.; Creminon, C.; Grassi, J.; Wagner, A.; Mioskowski, C. Angew. Chem., Int. Ed. 2002, 41, 124-127
61. Vedejs, E.; Jure, M. Angew. Chem., Int. Ed. 2005, 44, 3974-4001
62. Zhou, H.; Xu, Q.; Chen, P. Tetrahedron 2008, 64, 6494-6499