Synthesis of enol and vinyl esters catalyzed by an iridium complex

Tetrahedron Letters

Volumn 44, Issue 1, 2003, Pages 103-106

  Nakagawa, Hideto ^a   Okimoto, Yoshio ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

Alkyne; Carboxylic acid; Enol ether; Iridium; Vinyl acetate; Vinyl ether

Indexed keywords

ALKYNE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; IRIDIUM COMPLEX; SODIUM CARBONATE; SODIUM DERIVATIVE; VINYL ACETATE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; TRANSVINYLATION;

EID: 0037212998     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02451-6     Document Type: Article

References (37)

1. March J. Advanced Organic Chemistry. 1985;Wiley, New York.
2. Monthéard J.P., Camps M., Seytre G., Guillet J., Dubois J.C. Makromol. Chem. 72:1978;45.
3. (a) Lobell, M.; Schneider, M.P. Synthesis. 1994, 375;
4. (b) Seidel, A.; Jägers, E.; Bylsma, F. Eur. Pat. 0574725 A1, 1993.
5. (c) Murray, E.R.; Lincoln, D.M. Catal. Today. 1992, 13, 93;
6. (d) Murray, R. E. Eur. Pat. 0351603 A2, 1989.
7. (e) Mondal M.A.S., van der Meer R., German A.L., Heikens D. Tetrahedron. 1974;4205.
8. (f) Henry, P.M. Acc. Chem. Res. 1973, 6, 16.
9. (g) Rothman E.S., Serota S., Swern D. J. Org. Chem. 1966, 31, 629.
10. Nicoleau, I.; Colling, P.; Johnson, L. Int. Pat. WO 94/08714, 1994.
11. Colquhoun H.M., Holton J., Thompson D.J., Twigg M.V. New Pathways for Organic Synthesis. 1985;350 Plenum Press, New York.
12. Schultz R.G., Gross D.E. Adv. Chem. Ser. 70:1968;97.
13. Kitching W., Rapport Z., Winstein S., Young W.G. J. Am. Chem. Soc. 88:1966;2054.
14. Hudrlik P.F., Hudrlik A.M. J. Org. Chem. 38:1973;4254.
15. Rotem M., Shvo Y. Organometallics. 2:1983;1689.
16. Kawano H., Masaki Y., Matsunaga T., Hiraki K., Onishi M., Tsubomura T. J. Orgnometallic Chem. 604:2000;69.
17. Bruneau C., Dixneuf P.H. Chem. Commun. 1997;507.
18. Doucet H., Martin-Vaca B., Bruneau C., Dixneuf P.H. J. Org. Chem. 60:1995;7247.
19. Kita Y., Maeda H., Onari K., Okuno T., Tamura Y. J. Chem. Soc., Perkin Trans. 1. 1993;2999.
20. Bruneau C., Neveux M., Kabouche Z., Ruppin C., Dixneuf P.H. Synlett. 1991;755.
21. Söderberg B.C., Turbeville M.J. Organometallics. 10:1991;3951.
22. Ruppin C., Dixneuf P.H., Lecolier S. Tetrahedron Lett. 29:1988;5365.
23. Mitsudo T., Hori Y., Yamakawa Y., Watanabe Y. J. Org. Chem. 52:1987;2230.
24. Ruppin C., Dixneuf P.H. Tetrahedron Lett. 27:1986;6323.
25. Mitsudo T., Hori Y., Watanabe Y. J. Org. Chem. 50:1985;1566.
26. Lu X., Zhu G., Ma S. Tetrahedron Lett. 33:1992;7205.
27. Bianchini C., Meli A., Peruzzini M., Zanobini F., Bruneau C., Dixneuf P.H. Organometallics. 9:1990;1155.
28. Okimoto Y., Sakaguchi S., Ishii Y. J. Am. Chem. Soc. 124:2002;1590.
29. Sakaguchi S., Kubo T., Ishii Y. Angew. Chem., Int. Ed. Engl. 40:2001;2534.
30. Sakaguchi S., Yamaga T., Ishii Y. J. Org. Chem. 66:2001;4710.
31. Higashino T., Sakaguchi S., Ishii Y. Org. Lett. 2:2000;4193.
32. Kubo T., Sakaguchi S., Ishii Y. Chem. Commun. 2000;625.
33. 3 (0.02 mmol) were added 1 (1 mmol) and 2 (2 mmol) under Ar. The reaction mixture was stirred at 100°C for 15 h. After quenching with wet ether, the product was isolated by column chromatography (230-400 mesh silica gel).
34. Ohmura T., Yorozuya S., Yamamoto Y., Miyaura N. Organometallics. 19:2000;365.
35. 13.
36. Tani, K.; Hoshida, K.; Yamagata, T. In Symposium on Organometallic Chemistry, Japan, Abstract, 2001, 168.
37. 2 (0.01 mmol) and NaOAc (0.03 mmol) were added 26 (1 mmol) and 25 (10 mmol) under Ar. The reaction mixture was stirred at 100°C for 15 h.