C-C double bond cleavage of linear α,β-unsaturated ketones

Bulletin of the Korean Chemical Society

Volumn 25, Issue 11, 2004, Pages 1623-1624

  Lim, Sung Gon ^a   Jun, Chul Ho ^a  

^a Yonsei University   (South Korea)

Author keywords

C C Double bond cleavage; C H bond activation; Rhodium catalyst; , Unsaturated ketone

Indexed keywords

2 AMINOPYRIDINE DERIVATIVE; ALKENE; BENZOIC ACID; BENZYLAMINE; CYCLOHEXYLAMINE; KETONE DERIVATIVE; PICOLINE DERIVATIVE;

ALKYLATION; ARTICLE; CHELATION; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; DEGRADATION; FRAGMENTATION REACTION; HYDROGEN BOND; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

EID: 10644246751     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2004.25.11.1623     Document Type: Article

References (28)

1. (a) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101.
2. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879-2932.
3. (c) Dyker, G. Angew. Chem. Int. Ed. 1999, 38, 1698-1712.
4. (d) Ritleng, V.; Claude, S.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769.
5. (e) Kakiuchi, F.; Murai, S. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, German, 1999; pp 47-79.
6. (f) Saillard, J.-Y.; Hoffmann, R. J. Am. Chem. Soc. 1984, 106, 2006-2026.
7. (g) Sakaki, S. Bull. Korean Chem. Soc. 2003, 24, 829-831.
8. (a) Jun, C.-H.; Chung, K.-W.; Hong, J.-B. Org. Lett. 2001, 3, 785-787.
9. (b) Jun, C.-H.; Lee, D.-Y.; Lee, H.; Hong, J.-B. Angew. Chem. Int. Ed. 2000, 39, 3070-3072.
10. (c) Jun, C.-H.; Lee, H.; Park, J.-B.; Lee, D.-Y. Org. Lett. 1999, 1, 2161-2164.
11. (d) Jun, C.-H.; Hong, J.-B. Org. Lett. 1999, 1, 887-889.
12. (e) Kim, J.-H.; Jun, C.-H. Bull. Korean Chem. Soc. 1999, 20, 27-29.
13. (f) Jun, C.-H.; Huh, C.-W.; Na, S.-J. Angew. Chem. Int. Ed. 1998, 37, 145-147.
14. (g) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200-1201.
15. (h) Jun, C.-H.; Lee, D.-Y.; Hong, J.-B. Tetrahedron Lett. 1997, 38, 6673-6676.
16. (a) Jun, C.-H.; Hong, J.-B.; Kim, Y.-H.; Chung, K.-W. Angew. Chem. Int. Ed. 2000, 39, 3440-3442.
17. (b) Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-W.; Kim, Y.-H. Chem. Eur. J. 2002, 8, 485-492.
18. (a) Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489.
19. (b) Lee, D.-Y.; Lim, Y.-G.; Jun, C.-H. Bull. Korean Chem. Soc. 1997, 18, 824-827.
20. (c) Lee, D.-Y.; Jun, C.-H. Bull. Korean Chem. Soc. 2003, 24, 1059-1060.
21. Jun, C.-H.; Lee, H.; Moon, C. W.; Hong, H.-S. J. Am. Chem. Soc. 2001, 123, 8600-8601.
22. Lee, D.-Y.; Hong, B.-S.; Cho, E.-G.; Lee, H.; Jun, C.-H. J. Am. Chem. Soc. 2003, 125, 6372-6373.
23. Jun, C.-H.; Moon, C. W.; Lim, S.-G.; Lee, H. Org. Lett. 2002, 4, 1595-1597.
24. Jun, C.-H.; Moon, C. W.; Kim, Y.-M.; Lee, H. Tetrahedron Lett. 2002, 43, 4233-4236.
25. 4, and the ratio of 7 and 8 was determined by integration in gas chromatography (GC). The reaction mixture was purified by column chromatography (n-hexane: ethyl acetate = 5: 1) to give 7 and 8.
26. (a) Eisch, J. J.; Sanchez, R. J. Org. Chem. 1986, 51, 1848-1852.
27. (b) Yamagami, C.; Weisbuch, F.; Dana, G. Tetrahedron 1971, 27, 2967-2975.
28. Preparation of intermediate α,β-unsaturated ketimine 9a: the reaction mixture of 1a (2.00 g, 13.7 mmol) and 5a (1.36 g, 13.7 mmol) was stirred in the presence of molecular sieves at room temperature for 15 h. After the reaction, the mixture was filtered on a sinter glass to remove molecular sieves. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by kugelrohr distillation to afford 1.25 g (40%) of α,β-unsaturated ketimine 9a.