Investigation of substrate-selectivity pattern in the oxidation of secondary alcohols by amino acid-derived IBX derivatives

Arkivoc

Volumn 2005, Issue 1, 2005, Pages 143-153

  Kuhakarn, Chutima ^a   Kittigowittana, Krisada ^a   Pohmakotr, Manat ^a   Reutrakul, Vichai ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Hypervalent iodine; IBX amide; Oxidation

Indexed keywords

ALCOHOL; AMINO ACID; BENZAMIDE DERIVATIVE; KETONE;

ALCOHOL OXIDATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; ENZYME SPECIFICITY; REACTION ANALYSIS; SYNTHESIS;

EID: 15444362655     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (53)

1. Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 343, 5.
2. (a) Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 2003, 125, 4166.
3. (b) Jeong, K.-S.; Kim, S.-H.; Park, H.-J.; Chang, K.-J.; Kim, K. S. Chem. Lett. 2002, 1114.
4. (c) Lin, M.-H.; Rajanbabu, T. V. Org. Lett. 2002, 4, 1607.
5. (d) Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496.
6. (e) Bellemin-Laponnaz, S.; Tweddell, J.; Ruble, J. C., Breitling, F. M.; Fu, G. C. Chem. Commun. 2000, 1009.
7. (f) Spivey, A. C.; Fekner, T.; Spey, S. E. J. Org. Chem. 2000, 65, 3154.
8. (g) Naraku, G.; Shimomoto, N.; Hanamoto, T.; Inanaga, J. Enantiomer 2000, 5, 135.
9. (h) Lee, D.; Huh, E. A.; Kim, M.-J.; Hyun, M.; Koh, J. J.; Park, J. Org. Lett. 2000, 2, 2377.
10. (i) Yamada, S.; Katsumata, H. J. Org. Chem. 1999, 64, 9365.
11. (j) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 265.
12. (k) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794.
13. (l) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629.
14. (m) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492.
15. (n) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169.
16. (a) Bagdanoff, J. T.; Stoltz, B. M. Angew. Chem. Int. Ed. 2004, 43, 353.
17. (b) Mandal, S. K.; Sigman, M. S. J. Org. Chem. 2003, 68, 7535.
18. (c) Nishibayashi, Y.; Yamauchi, A.; Onodera, G.; Uemura, S. J. Org. Chem. 2003, 68, 5875.
19. (d) Sun, W.; Wang, H.; Xia, C.; Li, J.; Zhao, P. Angew. Chem. Int. Ed. 2003, 42, 1042.
20. (e) Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119.
21. (f) Gross, Z.; Ini, S. Org. Lett. 1999, 1, 2077.
22. (g) Hashiguchi, S.; Fujii, A.; Haack, K.-J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem. Int. Ed. 1997, 36, 288.
23. (h) Rychnovsky, S. D.; McLernon, T. L.; Rajapakse, H. J. Org. Chem. 1996, 61, 1194.
24. Martin, V. S.; Woodward, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
25. (a) Hartmann, C.; Meyer, V. Chem. Ber. 1893, 26, 1727.
26. (b) Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
27. (c) Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272.
28. (d) De Munari, S.; Frigerio, M.; Santagostino, M. J. Org. Chem. 1996, 61, 9272.
29. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
30. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
31. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
32. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
33. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
34. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
35. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
36. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
37. For an overview see: Wirth, T. Angew. Chem. Int. Ed. 2001, 40, 2812. For recent developments see: (a) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192. (b) Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed. 2003, 42, 4077. (c) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (d) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245. For recent oxidative deprotection see: (e) Wu, Y.; Shen, X.; Huang, J.-H.; Tang, C.-J.; Liu, H.-H.; Hu, Q. Tetrahedron Lett. 2002, 43, 6443. (f) Wu, Y.; Huang, J.-H.; Shen, X.; Hu, Q.; Tang, C.-J. Li, L. Org. Lett. 2002, 4, 2141. For α-functionalizaition of ketones see: (g) Pan, Z.; Liu, X.; Liang, Y. Tetrahedron Lett. 2004, 45, 4101. For oxidative cleavage see: (h) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 9119.
38. (a) Ozzane, A.; Pouysegu, L.; Depernet, D.; Francois, B.; Quideau, S. Org. Lett. 2003, 5, 2903.
39. (b) Thottumkara, A. P.; Vinod, T. K. Tetrahedron Lett. 2002, 43, 569.
40. (a) Zhdankin, V. V.; Koposov, A. Y.; Netzel, B. C.; Yashin, N. V.; Rempel, B. P.; Freguson, M. J. Tykwinski, R. R. Angew. Chem. Int. Ed. 2003, 42, 2194.
41. (b) Zhdankin, V. V.; Smart, J. T.; Zhao, P.; Kiprof, P. Tetrahedron Lett. 2000, 41, 5299.
42. (a) Imamoto, T.; Koto, H. Chem. Lett. 1986, 967.
43. (b) Ray, D. G.; Koser, G. F. J. Am. Chem. Soc. 1990, 112, 5672.
44. (c) Ochiai, M.; Takaoda, Y.; Masaki, Y.; Nagao, Y.; Shiro, M. J. Am. Chem. Soc. 1990, 112, 5677.
45. (d) Hatzigrigoriou, E.; Varvoglis, A.; Bakola-Christianopoulou, M. J. Org. Chem. 1990, 55, 315.
46. (e) Ray, D. G.; Koser, G. F. J. Org. Chem. 1992, 57, 1607.
47. (f) Stickley, S. H.; Martin, J. C. Tetrahedron Lett. 1995, 36, 9117.
48. (g) Rabah, G. A.; Koser, G. F. Tetrahedron Lett. 1996, 37, 6453.
49. (h) Zhdankin, V. V.; Krasutsky, A. P.; Kuehl, C. J.; Simonsen, A. J.; Woodward, J. K.; Mismash, B.; Bolz, J. T. J. Am. Chem. Soc. 1996, 118, 5192.
50. (i) Zhdankin, V. V.; Kuehl, C. J.; Krasutsky, A. P.; Bolz, J. T.; Simonsen, A. J. J. Org. Chem. 1996, 61, 6547.
51. (j) Wirth, T.; Hirt, U. H. Tetrahedron Asymmetry 1997, 8, 23.
52. (k) Kürti, L.; Herczegh, P.; Visy, J.; Simonyi, M.; Antus, S.; Pelter, A. J. Chem. Soc., Perkin Trans. 1, 1999, 379.
53. Munari, S. D.; Frigerio, M.; Santagostino, M. J. Org. Chem. 1996, 61, 9272.