Practical method for transforming alkynes into α-diketones

Journal of Organic Chemistry

Volumn 71, Issue 2, 2006, Pages 826-828

  Wan, Zhonghui ^a   Jones, Chauncey D ^a   Mitchell, David ^a   Pu, John Y ^a   Zhang, Tony Y ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; HYDRATION; HYDROCARBONS; KETONES; RATE CONSTANTS; REACTION KINETICS;

ALKYNES; BRØNSTED ACID-PROMOTED "HYDRATION"; DMSO; OXIDATION SEQUENCES;

OXIDATION;

ACID; ALKYNE DERIVATIVE; BRONSTED ACID; CARBONYL DERIVATIVE; DIKETONE; DIMETHYL SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; HYDRATION; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS;

ALKYNES; DIMETHYL SULFOXIDE; INDICATORS AND REAGENTS; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDATION-REDUCTION;

EID: 30744474215     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051793g     Document Type: Article

References (29)

1. (a) Babudri, F.; Fiaiulanese, V.; Mitrchese, G.; Punazi, A. Tetrahadron Lett. 1995, 40, 7305-7308 and references cited therein,
2. (b) De Kimpe, N.; Stanoeva, E.; Boeykens, M. Synthesis 1994, 427-431 und references eited therein.
3. (a) Bartn, T. E.; Stealey, M. A.; Collins, P. W.; Weier, R. M. Bioorg. Med. Chem. Lett. 1998, 8, 3443-3448.
4. (b) Callahan, J. M.; Burgess, J. L.; Fernwahl, J. A.; Gasler, L. M., Harling, J. D.; Harrington, F. P.; Heer, J.; Kwon, C.; Lehr, R.; Mathur, A.; Olson, B. A.; Weinstoek, J.; Laping, N. J. J. Med. Chem. 2002, 45, 999-1001.
5. (c) McKenna, J. M.; Halley, F.; Souness, J. E.; McLay, I. M.; Piekett, S. D.; Collis, A. J.; Page, K.; Ahmed, I. J. Med. Chem. 2002, 45, 2173.
6. (d) Singh, S. K.; Saibaba, V.; Ravikumar, V.; Rudrttwar, S. V.; Daga, P.; Rao, C. S.; Akhila, V.; Hegde, P.; Rao, Y. K. Bioorg. Med. Chem. 2004, 12, 1881-1893.
7. Katritzky, A. R.; Zhang, D.; Kirichenko, K. J. Org. Chem. 2005, 70, 3271-3274 and references therein.
8. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N, Synthesis 1980, 8, 627-630.
9. (a) Srinvasan, N. S.; Lee, D. G. J. Org. Chem. 1979, 44, 1574.
10. (b) Lee, D. O.; Chang, V. S.; Chandler, W. D. J. Org. Chem. 1985, 50, 4306.
11. (a) Wolfe, S.; Pilgrim, W. R.; Oarrail, T. F.; Chamberlain, P. Can. J. Chem. 1971, 49, 1099-1015.
12. (b) Yusubov, M. S.; Filimonov, V. D.; Vasilyeva, V. P.; Chi, K. W. Synthesis 1995, 1234-1236.
13. (a) Zhu, Z. L.; Espenson. J. H. J. Org. Chem. 1995, 60, 7728-7732.
14. (b) Yusubov, M. S.; Zholobova, G. A.; Vasilevsky, S. F.; Tretyakov, E. V.; Knight, D. W. Tetrahedron 2002, 58, 1607-1610 and references therein.
15. Favino, T. F.; Fronza, G.; Fuganti, C.; Fuganti, D.; Grasselli, P.; Mele, A. J. Org. Chem. 1996, 61, 8975-8979.
16. (a) Kozhevnikov, I. V. Chem. Rev, 1998, 98, 171.
17. (b) Tsuchimoto, T.; Joya, T.; Shiraknwa, E.; Kawakami, Y. Synlett 2000, 12, 1777-1778.
18. Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563-4565 and references therein.
19. (a) Menashe, N.; Shvo, Y. J. Org. Chem. 1991, 56, 2912-2914.
20. (b) Menashe, N.; Shvo, Y. J. Org. Chem. 1993, 58, 7434-7439.
21. (a) Rabjohn, N. Org. React. 1949, 5, 331.
22. (b) Rabjohn, N. Org. React. 1976, 24, 261.
23. (c) Wentzel, B. B.; Donners, M. P. J.; Alsters, P. L.; Feiters, M. C.; Nolte, R. J. M. Tetrahedron 2000, 56, 7797-7803.
24. (d) Tatsugi, J.; Izawa, Y. J. Chem. Res., Miniprint 1988, 11, 2747-2763.
25. (e) Bonadies, F.; Bonini, C. Synth. Comman. 1988, 18, 1573-1580.
26. Kornblum, N.; Powers, J. W.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O.; Weaver, W. M. J. Am. Chem. Soc. 1957, 79, 6562.
27. Floyd, M. B.; Du, M. T.; Fabio, P. F.; Jacob, L. A.; Johnson, B. D. J. Org. Chem. 1985, 50, 5022-5027.
28. The efficient removal of the generated dimethyl sulfide by distillation from the reaction system is crucial for reaction completion. See Supporting Information.
29. Chow, Y. L.; Bakker, B. H. Can. J. Chem. 1982, 60, 2268-2273.