One-pot synthesis of oxo acid derivatives by RhI-catalyzed chelation-assisted hydroacylation

European Journal of Organic Chemistry

Volumn , Issue 11, 2006, Pages 2504-2507

  Jo, Eun Ae ^a   Jun, Chul Ho ^a  

^a Yonsei University   (South Korea)

Author keywords

Acylation; C H activation; Homogeneous catalysis; Rhodium

Indexed keywords

EID: 33744957211     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600236     Document Type: Article

References (39)

1. a) Y. S. Rao, Chem. Rev. 1976, 76, 625-694;
2. b) T. Ohkuma, M. Kitamura, R. Noyori, Tetrahedron Lett. 1990, 31, 5509-5512;
3. c) R. Frenette, M. Monette, M. A. Bernstein, R. N. Young, T. R. Verhoeven, J. Org. Chem. 1991, 56, 3083-3089;
4. d) K. M. Short, A. M. M. Mjalli, Tetrahedron Lett. 1997, 38, 359-362.
5. a) R. Ballini, G. Bosica, F. Gigli, Tetrahedron 1998, 54, 7573-7580;
6. b) R. Ballini, L. Baboni, G. Bosica, D. Fiorini, Synthesis 2002, 18, 2725-2728.
7. M. Yan, W.-J. Zhao, D. Huang, S.-J. Ji, Tetrahedron Lett. 2004, 45, 6365-6367.
8. E. Baciocchi, E. Muraglia, Tetrahedron Lett. 1994, 35, 2763-2766.
9. For intermolecular hydroacylation using various aldehydes, alcohol, and aldimines with alkenes, see: a) T. Kondo, M. Akazome, Y. Tsuji, Y. Watanabe, J. Org. Chem. 1990, 55, 1286-1291;
10. b) C. P. Lenges, P. S. White, M. Brookhart, J. Am. Chem. Soc. 1998, 120, 6965-6979;
11. c) T. Kondo, N. Hiraishi, Y. Morisaki, K. Wada, Y. Watanabe, T. Mitsudo, Organometallics 1998, 17, 2131-2134;
12. d) C.-H. Jun, C.-W. Huh, S.-J. Na, Angew. Chem. 1998, 110, 150-152;
13. Angew. Chem. Int. Ed. 1998, 37, 145-147;
14. e) C.-H. Jun, J.-B. Hong, Org. Lett. 1999, 1, 887-889;
15. f) M. Tanaka, M. Imai, Y. Yamamoto, K. Tanaka, M. Shimowatari, S. Nagumo, N. Kawahara, H. Suemune, Org. Lett. 2003, 5, 1365-1367.
16. a) K. Kokubo, K. Matsumasa, M. Miura, M. Nomura, J. Org. Chem. 1997, 62, 4564-4565;
17. b) C.-H. Jun, H. Lee, J.-B. Hong, B.-I. Kwon, Angew. Chem. 2002, 114, 2250-2251;
18. Angew. Chem. Int. Ed. 2002, 41, 2146-2147.
19. For recent reviews, see: a) D. Sames, in: Activation and Functionalization of C-H bonds (Eds.: K. I. Goldberg, A. S. Goldman), Ed. Am. Chem. Soc., Washington, DC, 2004, p. 155;
20. b) G. Dyker, Angew. Chem. 1999, 111, 1808-1822;
21. Angew. Chem. Int. Ed. 1999, 38, 1698-1712;
22. c) V. Ritleng, C. Sirlins, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1770;
23. d) F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077-1101.
24. a) M. C. Willis, S. J. McNally, P. J. Beswick, Angew. Chem. 2004, 116, 344-347;
25. Angew. Chem. Int. Ed. 2004, 43, 340-343;
26. b) M. C. Willis, H. E. Randell-Sly, R. L. Woodward, G. S. Currie, Org. Lett. 2005, 7, 2249-2251.
27. M. C. Willis, S. Sapmaz, Chem. Commun. 2001, 2558-2559.
28. a) C.-H. Jun, H. Lee, J.-B. Hong, J. Org. Chem. 1997, 62, 1200-1201;
29. b) C.-H. Jun, D.-Y. Lee, H. Lee, J.-B. Hong, Angew. Chem. 2000, 112, 3214-3216;
30. Angew. Chem. Int. Ed. 2000, 39, 3070-3072.
31. δ-Oxo esters could be prepared by coupling of acrylic esters and enolates, while ε-oxo esters could be prepared by ozonolyisis of 1-alkylcyclohexene. For the recent development of δ-oxo esters, see: M. Yasuda, K. Chiba, N. Ohigashi, Y. Katoh, A. Baba, J. Am. Chem. Soc. 2003, 125, 7291-7300.
32. For ε-oxo esters, see: Y.-S. Hon, K.-C. Wu, Tetrahedron 2003, 59, 493-498.
33. When the reaction of benzaldehyde (1a) and 1-hexene was carried out at 130°C in the presence of the same catalyst mixture for 1 h as in Table 1, heptanophenone was isolated in a 29% yield.
34. a) J. M. Brown, H. K. Kuok, Angew. Chem. 1996, 108, 679-682;
35. Angew. Chem. Int. Ed. Engl. 1996, 35, 657-659;
36. b) D. Tanaka, S. P. Romeril, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 10323-10333.
37. a) D. L. Reger, D. G. Garza, J. C. Baxter, Organometallics 1990, 9, 873-874;
38. b) C.-H. Jun, D.-C. Hwang, S.-J. Na, Chem. Commun. 1998, 1405-1406;
39. c) S.-G. Lim, J.-A. Ahn, C.-H. Jun, Org. Lett. 2004, 6, 4687-4690.