A straightforward synthesis of 4-hydroxy-(E)-2-alkenoic esters mediated by SmI2

Synlett

Volumn , Issue 5, 2001, Pages 627-628

  Kwon, Doo Won ^a   Cho, Min Seok ^a   Kim, Yong Hae ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

4 hydroxy (E) 2 alkenoic esters; Coupling reaction; Intermolecular manner; Propiolate ester

Indexed keywords

ALKENE DERIVATIVE; ESTER DERIVATIVE; KETONE; REDUCING AGENT; SAMARIUM DIIODIDE; TERT BUTYL ALCOHOL; TETRAHYDROFURAN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0342526899     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13391     Document Type: Article

References (32)

1. (a)Binder, M.; Tamm, C.; Angew. Chem., Int. Ed. Engl. 1973, 12, 370.
2. (b) Trost, B. M.; Rigby, J. H. J. Org. Chem. 1978. 43, 2938.
3. (c) Bartlett, P. A.; Green, F. G. J. Am. Chem. Soc. 1978, 700, 4858.
4. (d) Feldman, K. S.; Berven, H. M.; Romanelli, A. L. J. Org. Chem, 1993, 58, 6851.
5. (a) Curran, D. P. Synthesis 1988, 417 and 489.
6. (b) Iqbal, J.; Bahatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519.
7. (a) Bartlett, P. A. J. Am. Chem. Soc. 1976, 98, 3305.
8. (b) Tanikaga, R.; Nozaki, Y.; Tamura, T.; Kaji, A. Synthesis 1983, 134.
9. (c) Burgess, K.; Henderson, I. Tetrahedron Lett. 1989, 30, 4325.
10. Oritz de Montellano, P. R.; Hsu, C. K. Tetrahedron Lett. 1976, 4215.
11. Arcadi, A.; Cacchi, S.: Carelli, I.; Curulli, A.; Inesi, A.; Marinelli, F. Synlett 1990, 408.
12. Thijs, L.; Dommerholt, F. J.; Leemhuis, F. M. C.; Zwanenburg, B. Tetrahedron Lett. 1990, 31, 6589.
13. Recent reviews : (a) Molander, G. A. Chem. Rev. 1992, 92, 29.
14. (b) Molander, G. A. In Organic Reactions, Vol. 46; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1994, 211.
15. (c) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
16. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345.
17. (e) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321.
18. (f) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745 and references cited therein.
19. (a) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 5763.
20. (b) Ujikawa, O.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1989, 30, 2837.
21. (c) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1995, 60, 872.
22. (d) Molander, G. A.; Mckie, J. A. J. Org. Chem. 1994, 59, 3186.
23. (e) Molander, G. A.; McWilliams, J. C.; Noll, B. C. J. Am. Chem. Soc. 1997, 119, 1265.
24. (a) Inanaga, J.; Katsuki, J.; Ujikawa, O.; Yamaguchi, M. Tetrahedron Lett. 1991, 32, 4921.
25. (b) Baldwin, J. E.; Mackenzie Turner, S. C.; Moloney, M. G. Tetrahedron 1994, 50, 9425.
26. (c) Dinesh, C. U.; Reissig, H. U. Angew. Chem. Int. Ed. 1999, 38, 789.
27. (a) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236.
28. (b) Shim, S. C.; Hwang, J. T.; Kang, H. Y.; Chang, M. H. Tetrahedron Lett. 1990, 31, 4765.
29. (a) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M. J. Synlett 1992, 943.
30. (b) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6580.
31. Youn, S. W.; Park, H. S.; Kim, Y. H. Chem. Common. 2000, 2005.
32. 3: 186.1256, found 186. 1245.