TEMPO/NaIO4-SiO2: A catalytic oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated ketones

Organic Letters

Volumn 10, Issue 21, 2008, Pages 4715-4718

  Shibuya, Masatoshi ^a   Tomizawa, Masaki ^a   Iwabuchi, Yoshiharu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; AMINE OXIDE; KETONE; PERIODATE; PERIODIC ACID; PROPANOL; SILICON DIOXIDE; TEMPO; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALKYLATION; CATALYSIS; CYCLIC N-OXIDES; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PERIODIC ACID; PROPANOLS; SILICON DIOXIDE;

EID: 58149147192     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801673r     Document Type: Article

References (55)

1. (a) Babler, J. H.; Coghlan, M. J. Synth. Commun. 1976, 6, 469-474.
2. (b) Dauben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682-685.
3. (c) Sundararaman, P.; Hertz, W. L. J. Org. Chem. 1977, 42, 813-819.
4. For a recent review on an oxochromium(VI)-based oxidant, see: Luzzio, F. A. Org. React. 1998, 53, 1-221.
5. (a) Takano, S.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1989, 271-272.
6. (b) Majetich, G.; Lowery, D.; Khetani, V. Tetrahedron Lett. 1990, 31, 51-54.
7. (c) Luzzio, F. A.; Moor, W. J. J. Org. Chem, 1993, 58, 2966-2971.
8. (d) Majetich, G.; Song, J.-S.; Leigh, A. J.; Condon, S. M. J. Org. Chem. 1993, 58, 1030-1037.
9. (e) Guevel, A.-J.; Hart, D. J. J. Org. Chem. 1996, 61, 465-472.
10. (f) Trost, B. M.; Pinkerton, A. B. Org. Lett. 2000, 2, 1601-1603.
11. (g) Piers, E.; Walker, S. D.; Armbrust, R. J. Chem. Soc., Perkin Trans. 1 2000, 635-637.
12. (h) Nagata, H.; Miyazawa, N.; Ogasawara, K. Chem. Commun. 2001, 1094-1095.
13. (i) Hanada, K.; Miyazawa, N.; Ogasawara, K. Org. Lett, 2002, 4, 4515-4517.
14. (j) Muratake, H.; Natsume, M. Tetrahedron Lett. 2002, 43, 2913-2917.
15. (k) Mohr, J. H.; Halcomb, R. L. J. Am. Chem. Soc. 2003, 125, 1712-1713.
16. (l) Bohno, M.; Imase, H.; Chida, N. Chem. Commun. 2004, 1086-1087.
17. (m) Domínguez, M.; Alvarez, R.; Martras, S.; Farrés, J.; Parés, X.; de Lera, A. R. Org. Biomol Chem. 2004, 2, 3368-3373.
18. (n) Mandal, M.; Yun, H.; Dudley, G. B.; Lin, S.; Tan, S. L.; Tan, D. S.; Danishefsky, S. J. J. Org. Chem. 2005, 70, 10619-10637.
19. (o) Fernández-Mateos, A.; Silvo, A. I. R.; González, R. R.; Simmonds, M. S. Tetrahedron 2006, 62, 7809-7816.
20. (p) Li, C.-C.; Wang, C.-H.; Liang, B.; Zang, X.-H.; Deng, L.-J.; Jiang, S.; Chen, J.-H.; Wu, Y.-D.; Yang, Z. J. Org. Chem. 2006, 71, 6892-6897.
21. (q) Chavan, S. P.; Thakkar, M.; Jogdand, G. F.; Kalkote, U. R. J. Org, Chem, 2006, 71, 8986-8988.
22. (r) Shimizu, N.; Mizaguchi, A.; Murakami, K.; Noge, K.; Mori, N.; Nishida, R.; Kuwahara, Y. J. Pestic. Sci. 2006, 31, 311-315.
23. (s) Tanimoto, H.; Kato, T.; Chida, N. Tetrahedron Lett. 2007, 48, 6267-6270.
24. Shibuya, M.; Ito, S.; Takahashi, M.; Iwabuchi, Y. Org. Lett. 2004, 6, 4303-4306.
25. Shibuya, M.; Tomizawa, M.; Iwabuchi, Y. J. Org. Chem. 2008, 73, 4750-4752.
26. (a) de Nooy, A. E.; Besemer, A. C.; van Bekkum, H. Synthesis 1996, 1153-1174.
27. (b) Sheldon, R. A.; Arends, I. W. C. E. Adv. Synth. Catal. 2004, 346, 1051-1071.
28. Shibuya, M.; Tomizawa, M.; Suzuki, I.; Iwabuchi, Y. J. Am. Chem. Soc. 2006, 128, 8412-8413.
29. (a) Kagiya, T.; Kumuro, C.; Sakano, K.; Nishimoto, S. Chem. Lett. 1983, 365-368.
30. (b) Bobbitt, J. M.; Flores, M. C. L. Heterocycles 1988, 27, 509-533.
31. (c) Bobbitt, J. M.; Guttermuth, M. C. F.; Ma, Z.; Tang, H. Heterocycles 1990, 30, 1131-1140.
32. (d) Ma, Z.; Bobbitt, J. M. J. Org. Chem. 1991, 56, 6110-6114.
33. (e) Bobbitt, J. M. J. Org. Chem. 1998, 63, 9367-9374.
34. (f) Merbouh, N.; Bobbitt, J. M.; Bruckner, C. J. Org. Chem. 2004, 69, 5116-5119.
35. (a) Golubev, V. A.; Rozantsev, E. G.; Neiman, M. B. Bull Acad. Sci. U.S.S.R., Chem. Sci. 1965, 11, 1898-1904.
36. (b) Zhdanov, R. I.; Golubev, V. A.; Rozantsev, É. G. Bull. Acad. Sci. U.S.S.R., Chem. Ser. 1970, 19, 186-187.
37. (c) Golubev, V. A.; Zhdanov, R. I.; Rozantsev, É. G. Bull Acad. Sci. U.S.S.R., Chem. Ser. 1970, 19, 188-190.
38. During the preparation of our manuscript for publication, the catalytic oxidative rearragement of tertiary allylic alcohols by the Lewis acid/TEMPO/PhIO system was reported: Vatéle, J. M. Synlett 2008, 1785-1788.
39. De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974-6977.
40. 2 oxidation in complex natural product synthesis, see: (a) Mandal, M.; Yun, H.; Dudley, G. B.; Lin, D.; Tan, D. S.; Danishefsky, S. J. J. Org. Chem. 2005, 70, 10619-10637.
41. (b) Nicolaou, K. C.; Kofitis, T. V.; Vyskocil, S.; Petrovic, G.; Tang, W.; Frederick, M. O.; Chen, D. Y.-K.; Li, Y.; Ling, T.; Yamada, Y. M. A. J. Am. Chem. Soc. 2006, 128, 2859-2872.
42. (c) Paterson, I.; Ashton, K.; Britton, R.; Cecere, G.; Chouraqui, G.; Florence, G. J.; Stafford, J. Angew. Chem., Int. Ed. 2007, 46, 6167-6171.
43. 2 gave the clean spot of the desired product although the reaction was sluggish. See the Supporting Information.
44. 2 and obtained 1b in 24% yield from multiple spots of the reaction pruducts. See the Supporting Information for details.
45. Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-2562.
46. Bolm, C.; Magnus, A. S.; Hildebrand, J. P. Org. Lett. 2000, 2, 1173-1175.
47. Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285-287.
48. (a) Lei, M.; Hu, R.-J.; Wang, Y.-G. Tetrahedron 2006, 62, 8928-8932.
49. (b) Liu, Z.-Q.; Shang, X.; Chai, L.; Sheng, Q. Catal. Lett. 2008, 123, 317-320.
50. (a) Daumas, M.; Vo-Quang, Y.; Vo-Quang, L.; Le Goffic, F. Synthesis 1989, 64-65.
51. (b) Zhong, Y.-L.; Shing, T. K. M. J. Org. Chem. 1997, 62, 2622-2624.
52. (c) Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003, 1896-1897.
53. Tello-Aburto, R.; Ochoa-Teran, A.; Olivo, H. F. Tetrahedron Lett. 2006, 47, 5915-5917.
54. 2O prolonged the reaction time. Thus it was possible that water contained in silica gel would retard the reaction.
55. -].