Pentanidium-catalyzed enantioselective α-hydroxylation of oxindoles using molecular oxygen

Organic Letters

Volumn 14, Issue 18, 2012, Pages 4762-4765

  Yang, Yuanyong ^a   Moinodeen, Farhana ^a   Chin, Willy ^a   Ma, Ting ^a   Jiang, Zhiyong ^b   Tan, Choon Hong ^b,c  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b HENAN UNIVERSITY   (China)

^c Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

2-OXINDOLE; INDOLE DERIVATIVE; OXINDOLE; OXYGEN; PHOSPHITE; TRIETHYL PHOSPHITE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROXYLATION; STEREOISOMERISM;

CATALYSIS; HYDROXYLATION; INDOLES; MOLECULAR STRUCTURE; OXYGEN; PHOSPHITES; STEREOISOMERISM;

EID: 84868247526     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302030v     Document Type: Article

References (38)

1. Punniyamurthy, T.; Subbarayan, V.; Javed, I. Chem. Rev. 2005, 105, 2329-2363.
2. (a) Jones, A. B. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon Press, Ltd.: Oxford, 1991; Vol. 7, pp 151-191.
3. (b) Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E.Organic Reactions; Overman, L. E., Ed.; John Wiley & Sons, Inc.: New York, 2003; Vol. 62, pp 1-356.
4. (c) Christoffers, J.; Baro, A.; Werner, T. Adv. Synth. Catal. 2004, 346, 143-151.
5. (a) Doering, W. E.; Haines, R. M. J. Am. Chem. Soc. 1954, 76, 482-486.
6. (b) Gardner, J. N.; Carlona, F. E.; Gnoj, O. J. Org. Chem. 1968, 33, 3294-3297.
7. (c) Paquette, L. A.; DeRussy, D. T.; Pegg, N. A.; Taylor, R. T.; Zydowsky, T. M. J. Org. Chem. 1989, 54, 4576-4581.
8. (d) Konen,D.A.; Silbert,L. S.; Pfeffer, P.E. J. Org. Chem. 1975, 40, 3253-3258.
9. (e) Gardner, J. N.; Popperf, L.; Carlon, E.; Gnoj, O.; Herzog, H. L. J. Org. Chem. 1968, 33, 3695-3699.
10. (f) Lubin,H.; Tessier, A.; Chaume, G.; Pytkowicz, J.; Brigaud, T. Org. Lett. 2010, 12, 1496-1499.
11. (a) Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 4222-4266.
12. (b) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656-5682.
13. (c) Provencher, B. A.; Bartelson, K. J.; Liu, Y.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2011, 50, 10565-10569.
14. (d) Denmark, S. E.; Gould, N. D.; Wolf, L. M. J. Org. Chem. 2011, 76, 4260-4336.
15. (e) Denmark, S. E.; Gould, N. D.; Wolf, L. M. J. Org. Chem. 2011, 76, 4337-4357.
16. (a) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835-2838.
17. (b) Dehmlow, E. V.; Wagner, S.; Mulller, A. Tetrahedron 1999, 55, 6335-6346.
18. (c) Eckehard, V. D.; Stephanie, D.; Beate, N.; Stammler, H.-G. Eur. J. Org. Chem. 2002, 2087-2093.
19. (a) Eckehard, V. D.; Volker, K. Liebigs Ann. Chem. 1992, 283-285.
20. (b) Vries, E. F. J.; Ploeg, L.; Colao, M.; Brussee, J.; Van der Gen, A. Tetrahedron: Asymmetry 1995, 6, 1123-1132.
21. (a) Satyamaheshwar, P. Curr. Bioact. Compd. 2009, 5, 20-38.
22. (b) Piyasena, H.; Nicholas, A. M. Bioorg. Med. Chem. Lett. 1997, 7, 1255-1260.
23. (c) Zhang, H.; Kamano, Y.; Yoshitatsu, I.; Haruhisa, K.; Kanki, K.; Hideji, L.; George, R. P. Tetrahedron 1995, 51, 5523-5528.
24. (d) Teruhisa, T.; Hume, W. E.; Takashi, U.; Kazuhiko, O.; Yasuyuki, U.; Kazuo, K.; Shinji, H.; Jun, N.; Hitoshi, S.; Mutsuo, T.; Hiroshi, N.; Ryu, N. J. Med. Chem. 2001, 44, 4641-4649.
25. (e) Piyasena, H.; Matthew, E.; Sandra, L. M.; Jay, K.; Harvey, W.; Christopher, G. B.; Debra, J. P.; Gao, Q.; Stella, H.; Valentin, K. G.; Nicholas, A. M. J. Med. Chem. 2002, 45, 1487-1499.
26. (f) Teruhisa, T.; Hume, W. E.; Nagamine, J.; Kawamura, T.; Mutsuo, T.; Nagata, R. Bioorg. Med. Chem. Lett. 2005, 15, 1789-1792.
27. (g) Eugenia, M. L.; Raquel, P. H.; Mathias, C. Nat. Prod. Rep. 2010, 27, 1138-1167.
28. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381-1407.
29. (a) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488-16489.
30. (b) Sano, D.; Nagata, K.; Itoh, T. Org. Lett. 2008, 10, 1593-1595.
31. (c) Bui, T.; Candeias, N. R.; Barbas, C. F., III J. Am. Chem. Soc. 2010, 132, 5574-5575.
32. Ma, T.; Fu, X.; Kee, C.; Zong, L.; Pan, Y.; Huang, K.-W.; Tan, C.-H. J. Am. Chem. Soc. 2011, 133, 2828-2831.
33. (a) Zhu, M.-K.; Zhao, J.-F.; Loh, T.-P. J. Am. Chem. Soc. 2010, 132, 6284-6285.
34. (b) Chuang, G. J.; Wang, W.; Lee, E.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 1760-1762.
35. (c) Chiba, S.; Zhang, L.; Lee, J.-Y. J. Am. Chem. Soc. 2010, 132, 7266-7267.
36. (e) Zhang, C.; Jiao, N. J. Am. Chem. Soc. 2010, 132, 28-29.
37. (a) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
38. (b) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.