Transition-metal-free superbase-promoted stereoselective α-vinylation of ketones with arylacetylenes: A general strategy for synthesis of β,γ-unsaturated ketones

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 6880-6886

  Trofimov, Boris A ^a   Schmidt, Elena Yu ^a   Zorina, Nadezhda V ^a   Ivanova, Elena V ^a   Ushakov, Igor A ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL AROMATICS; ARYLACETYLENES; CYCLOALIPHATIC; E CONFIGURATION; STEREO-SELECTIVE; UNSATURATED KETONES; VINYLATION;

KETONES; TRANSITION METALS;

ORGANIC COMPOUNDS;

(E) 1 (FURAN 2 YL) 4 PHENYLBUT 3 EN 1 ONE; (E) 1(4 FLUOROPHENYL) 4 PHENYLBUT 3 EN 1 ONE; (E) 1,4 DIPHENYL 3 BUTEN 1 ONE; (E) 1[1,1 BIPHENYL] 4 YL 4(4 PENTYLPHENYL) 3 BUTEN 1 ONE; (E) 2 STYRYLCYCLODODECANONE; (E) 2 STYRYLCYCLOHEXANONE; (E) 2,2 DIMETHYL 6 PHENYL 4 STYRYLHEX 5 EN 3 ONE; (E) 2,2 DIMETHYL 6 PHENYLHEX 5 EN 3 ONE; (E) 3 ETHYL 1 PHENYLHEPT 1 EN 4 ONE; (E) 3 ETHYL 1(3 METHOXYPHENYL) HEPT 1 EN 4 ONE; (E) 3 ISOPROPYL 5 PHENYLPENT 4 EN 2 ONE; (E) 4 PHENYL 1 THIOPHEN 2 YL 3 BUTEN 1 ONE; (E) 4 STYRYLNONAN 5 ONE; (E) 4(2,5 DIMETHYLPHENYL) 1 PHENYLBUT 3 EN 1 ONE; (E) 4(3 METHOXYPHENYL) 2 METHYL 1(THIOPHEN 2 YL) BUT 3 EN 1 ONE; (E) 5 PHENYLPENT 4 EN 2 ONE; (E) 5(3 METHOXYPHENYL) 3 METHYLPENT 4 EN 2 ONE; (E) 6 METHYL 1 PHENYLHEPT 1 EN 4 ONE; (E) 6(2,5 DIMETHYLPHENYL) 2,2 DIMETHYLHEX 5 EN 3 ONE; 4(4 METHOXYPHENYL) 1 PHENYLBUT 3 EN 1 ONE; 4,4' (1,4 PHENYLENE) BIS [1 (NAPHTHALEN 2 YL) BUT 3 EN 1 ONE]; ACETYLENE DERIVATIVE; ALIPHATIC KETONE; ARYLACETYLENE DERIVATIVE; BETA GAMMA UNSATURATED KETONE; CYCLOALIPHATIC KETONE; DIMETHYL SULFOXIDE; HETEROAROMATIC KETONE; KETONE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

ALKYNES; CATALYSIS; DIMETHYL SULFOXIDE; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84865254672     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301005p     Document Type: Article

References (39)

1. Radin, N. S. Drug Dev. Res. 2008, 69, 15
2. Ohtsuka, Y.; Sasahara, T.; Oishi, T. Chem. Pharm. Bull. 1982, 30, 1106 and references therein
3. Gohain, M.; Gogoi, B. J.; Prajapati, D.; Sandhu, J. S. New J. Chem. 2003, 27, 1038
4. Comprehensive Organic Functional Group Transformations II; Katritzky, A. R.; Taylor, R. J. K., Eds.; Elsevier: Amsterdam, 2005.
5. Iwasaki, M.; Morita, E.; Uemura, M.; Yorimitsu, H.; Oshima, K. Synlett 2007, 167
6. Chieffi, A.; Kamikawa, K.; Ahman, J.; Fox, J. M.; Buchwald, S. L. Org. Lett. 2001, 3, 1897
7. Huang, J.; Bunel, E.; Faul, M. M. Org. Lett. 2007, 9, 4343
8. Negishi, E.; Owezarczyk, Z. R.; Swanson, D. R. Tetrahedron Lett. 1991, 32, 4453
9. Yadav, J. S.; Reddy, B. V. S.; Reddy, M. S.; Parimala, G. Synthesis 2003, 2390
10. Larock, R. C.; Lu, Y. J. Org. Chem. 1993, 58, 2846
11. Lee, A. S.-Y.; Lin, L.-S. Tetrahedron Lett. 2000, 41, 8803
12. Ooi, T.; Goto, R.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 10494
13. Takami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2004, 6, 4555
14. Yasuda, M.; Tsuchida, M.; Baba, A. Chem. Commun. 1998, 563
15. Brown, H. C.; Soundararajan, R. Tetrahedron Lett. 1994, 35, 6963
16. Kosugi, M.; Naka, H.; Harada, S.; Sano, H.; Migita, T. Chem. Lett. 1987, 1371
17. Obora, Y.; Nakanishi, M.; Tokunaga, M.; Tsuji, Y. J. Org. Chem. 2002, 67, 5835
18. Obora, Y.; Ogawa, Y.; Imai, Y.; Kawamura, T.; Tsuji, Y. J. Am. Chem. Soc. 2001, 123, 10489
19. Hanzawa, Y.; Tabuchi, N.; Taguchi, T. Tetrahedron Lett. 1998, 39, 6249
20. Hanzawa, Y.; Narita, K.; Yabe, M.; Taguchi, T. Tetrahedron 2002, 58, 10429
21. Wang, J.-X.; Jia, X.; Meng, T.; Xin, L. Synthesis 2005, 2838
22. Trost, B. M.; Yang, H.; Thiel, O. R.; Frontier, A. J.; Brindle, C. S. J. Am. Chem. Soc. 2007, 129, 2206
23. Krishna, P. R.; Srinivas, R. Tetrahedron: Asymmetry 2008, 19, 1153
24. Zhang, M.; Jiang, H.; Dixneuf, P. H. Adv. Synth. Catal. 2009, 351, 1488
25. Omura, S.; Fukuyama, T.; Horiguchi, J.; Murakami, Y.; Ryu, I. J. Am. Chem. Soc. 2008, 130, 14094
26. Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120
27. Shibahara, F.; Krische, M. J. Chem. Lett. 2008, 37, 1102
28. Dalpozzo, R.; De Nino, A.; Bartoli, G.; Bosco, M.; Sambri, L.; Marcantoni, E. J. Org. Chem. 1998, 63, 3745
29. Nomura, K.; Matsubara, S. Synlett 2008, 1412
30. Moody, C. L.; Pugh, D. S.; Taylor, R. J. K. Tetrahedron Lett. 2011, 52, 2511
31. Favorsky, A. E. Zh. Russ. Khim. O-va. 1906, 37, 643
32. Smith, M.; March, J. March's Advanced Organic Chemistry, 6 th ed.; Wiley: New York, 2007; p 1360.
33. Trofimov, B. A.; Schmidt, E. Yu.; Ushakov, I. A.; Zorina, N. V.; Skital'tseva, E. V.; Protsuk, N. I.; Mikhaleva, A. I. Chem.-Eur. J. 2010, 16, 8516
34. Dickstein, J. I.; Miller, S. I. In The Chemistry of the Carbon-Carbon Triple Bond, Part 2; Patai, S., Ed.; Wiley: New York, 1978; p 813.
35. Nagayama, K.; Kumar, A.; Wutrich, K.; Ernst, R. R. J. Magn. Reson. 1980, 40, 321
36. Wagner, G.; Wutrich, K. J. Mol. Biol. 1982, 155, 347
37. Bodenhausen, G.; Ruben, D. J. Chem. Phys. Lett. 1980, 69, 185
38. Bax, A; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093
39. Dimethyl Sulfoxide (DMSO); Crown Zellerbach Chemical Products Division: Vancouver, WA, 1985; Technical Bulletin.