Unexpected formation of (E)-4-alkene 1,3-diketones from the three-component reaction of lithium selenolates with 1-(1-alkynyl)cyclopropyl ketones and aldehydes

Journal of Organic Chemistry

Volumn 76, Issue 14, 2011, Pages 5598-5605

  Xu, Jianfeng ^a   Wu, Luling ^a   Huang, Xian ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPYL KETONES; DOUBLE BONDS; GOOD YIELD; SINGLE BOND; STEREOSELECTIVE SYNTHESIS; THREE COMPONENT REACTIONS; THREE-COMPONENT;

ALDEHYDES; KETONES; LITHIUM; OLEFINS; STEREOCHEMISTRY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

1,3 DIKETONE; ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; ALKYNYL GROUP; CARBON; KETONE DERIVATIVE; LITHIUM DERIVATIVE; OXYGEN; SELENIUM;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CROSS COUPLING REACTION; ISOMERIZATION; OXIDATION; SONOGASHIRA REACTION; STEREOCHEMISTRY; SYNTHESIS; THREE COMPONENT REACTION;

ALDEHYDES; ALKENES; KETONES; LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SELENIUM; STEREOISOMERISM;

EID: 79960158654     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2005439     Document Type: Article

References (48)

1. Liu, H.-W.; Walsh, C. T. The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons Ltd.: New York, 1987; p 959.
2. Brackmann, F.; Meijere, A. Chem. Rev. 2007, 107, 4493
3. Reichelt, A.; Martin, S. F. Acc. Chem. Res. 2006, 39, 433
4. Reissig, H. U.; Zimmer, R. Chem. Rev. 2003, 103, 1151
5. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
6. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051
7. Hudlicky, T.; Reed, J. W. Angew. Chem., Int. Ed. 2010, 49, 4864
8. Corey, E. J.; Walinsky, S. W. J. Am. Chem. Soc. 1972, 94, 8932
9. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1973, 95, 5311
10. Wada, E.; Okawara, M.; Nakai, T. J. Org. Chem. 1979, 44, 2952
11. Kawai, T.; Ooi, T.; Kusumi, T. Chem. Pharm. Bull. 2003, 51, 291
12. Challand, B. D.; Hikino, H.; Kornis, G.; Lange, G.; de Mayo, P. J. Org. Chem. 1969, 34, 794
13. Warner, P. M.; Chen, B.-L.; Wada, E. J. Org. Chem. 1981, 46, 4795
14. Huang, X.; Yang, Y. Org. Lett. 2007, 9, 1667
15. Huang, X.; Zhou, H. Org. Lett. 2002, 4, 4419
16. Su, C.; Huang, X. Adv. Synth. Catal. 2009, 351, 135
17. Li, W.; Yuan, W.; Pindi, S.; Shi, M.; Li, G. Org. Lett. 2010, 12, 920
18. Lifchits, O.; Alberico, D.; Zakharian, I.; Charette, A. B. J. Org. Chem. 2008, 73, 6838
19. Mothe, S. R.; Chan, P. W. H. J. Org. Chem. 2009, 74, 5887
20. Cerat, P.; Gritsch, P. J.; Goudreau, S. R.; Charette, A. B. Org. Lett. 2010, 12, 564
21. Zhang, J.; Schmalz, H.-G. Angew. Chem,. Int. Ed. 2006, 45, 6704
22. Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814
23. Li, G.; Huang, X.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 6944
24. Zhang, Y.; Chen, Z.; Xiao, Y.; Zhang, J. Chem. - Eur. J. 2009, 15, 5208
25. Zhang, Y.; Liu, F.; Zhang, J. Chem. - Eur. J. 2010, 16, 6146
26. Bai, Y.; Fang, J.; Ren, J.; Wang, Z. Chem. - Eur. J. 2009, 15, 8975
27. Huang, X.; Fu, W.; Miao, M. Tetrahedron Lett. 2008, 49, 2359
28. Krause, N.; Hashmi, A. S. K. Modern Allene Chemistry; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1 - 2.
29. Ma, S. Chem. Rev. 2005, 105, 2829
30. Ma, S. Acc. Chem. Res. 2003, 36, 701
31. Ma, S. Acc. Chem. Res. 2009, 42, 1679
32. Ma, S. Aldrichim. Acta 2007, 40, 91
33. Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590
34. Brasholz, M.; Reissig, H. U.; Zimmer, R. Acc. Chem. Res. 2009, 42, 45
35. Chowdhury, M. A.; Reissig, H. U. Synlett 2006, 15, 2383
36. Banerjee, M.; Roy, S. Org. Lett. 2004, 6, 2137
37. Cristau, H.-J.; Viala, J.; Christol, H. Tetrahedron Lett. 1982, 23, 1569
38. Ma, S.; Y, S.; Li, L.; Tao, F. Org. Lett. 2002, 4, 505
39. Ma, S.; Y., S. Org. Lett. 2005, 7, 5063
40. Friedrich, L. E.; Schuster, G. B. J. Am. Chem. Soc. 1971, 93, 4602
41. Friedrich, L. E.; Schuster, G. B. J. Am. Chem. Soc. 1973, 95, 6869
42. Martino, P. C.; Shevlin, P. B. J. Am. Chem. Soc. 1980, 102, 5430
43. Calter, M. A.; Liao, W. J. Am. Chem. Soc. 2002, 124, 13127
44. Wu, T. S.; Leu, Y. L.; Chan, Y. Y.; Wu, P. L.; Kuoh, C. S.; Wu, S. J.; Wang, Y. Phytochemistry 1997, 45, 1393
45. Tanitame, A.; Oyamada, Y.; Ofuji, K.; Suzuki, K.; Ito, H.; Kawasaki, M.; Wachi, M.; Yamagishi, J. Bioorg. Med. Chem. Lett. 2004, 14, 2863
46. Solladie, G.; Gehrold, N.; Maignan, J. Eur. J. Org. Chem. 1999, 2309
47. Shi, H. P.; Wanibuchi, K.; Morita, H.; Endo, K.; Noguchi, H.; Abe, I. Org. Lett. 2009, 11, 551
48. Panda, B.; Sarkar, T. K. Tetrahedron Lett. 2010, 51, 301