Ring-opening of lactones with enolate nucleophiles: A simple access to functionalised β-ketoesters, β,δ-diketoesters and β-ketosulfoxides

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 619-622

  Lanners, Steve ^a   Khiri, Naïma ^a   Solladié, Guy ^a   Hanquet, Gilles ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Ketosulfoxides; Lactone ring opening

Indexed keywords

ESTER DERIVATIVE; LACTONE DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY;

EID: 11144329556     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.135     Document Type: Article

References (24)

1. T.M. Harris, and C.M. Harris Tetrahedron 33 1977 2159
2. J.S. Hubbard, and T.M. Harris J. Org. Chem. 46 1981 2566
3. G. Hanquet, F. Colobert, S. Lanners, and G. Solladié ARKIVOC vii 2003 328
4. S.N. Huckin, and L. Weiler Can. J. Chem. 52 1974 1343
5. C. Iwata, M. Fujita, T. Kuroki, K. Hattori, S. Uchida, and T. Imanishi Chem. Pharm. Bull. 36 1988 3257
6. T. Hanamoto, and T. Hiyama Tetrahedron Lett. 29 1988 6467
7. T.A. Oster, and T.M. Harris Tetrahedron Lett. 24 1983 1851
8. G. Solladié, M.C. Maestro, A. Rubio, C. Pedregal, M.C. Carreno, and J.L. Garcia-Ruano J. Org. Chem. 56 1991 2317
9. G. Hanquet, G. Solladié, and X.J. Salom-Roig Tetrahedron Lett. 41 2000 551 554
10. G. Hanquet, G. Solladié, and X.J. Salom-Roig Tetrahedron Lett. 41 2000 2737
11. A.J. Duggan, M.A. Adams, and J. Meinwald Tetrahedron Lett. 45 1978 4323
12. A.J. Duggan, M.A. Adams, and J. Meinwald Tetrahedron Lett. 19 1978 4327
13. B. Loubinoux, J.L. Sinnes, and A.C. O'Sullivan J. Chem. Soc., Perkin Trans. 1 1995 521
14. Tetrahedron 51 1995 3549 3558
15. R.E. Ireland, and P. Wipf Tetrahedron Lett. 30 1989 919
16. A.G.M. Barett, and R.A.E. Carr J. Org. Chem. 51 1986 4254
17. R.E. Dolle, and K.C. Nicolaou J. Am. Chem. Soc. 107 1985 1691
18. T.M. Wilson, P. Kocienski, K. Jarowicki, K. Isaac, A. Falk, S.F. Campbell, and J. Bordner Tetrahedron 46 1990 1757
19. F. Velazquez, and H.F. Olivo Org. Lett. 2 2000 1931 1934
20. M.Y. Rios, F. Velazquez, and H.F. Olivo Tetrahedron 59 2003 6531 6537
21. K. Ditrich, and R.W. Hoffmann Tetrahedron Lett. 26 1985 6325
22. 3): δ = 206.5, 169.8, 81.6, 72.4, 53.9, 37.0, 29.9, 29.6, 27.9, 25.9, 18.1, 12.8, 9.6, -4.5
23. 3): δ = 201.5, 142.1, 139.1, 130.1, 124.1, 68.1, 62.6, 62.6, 44.7, 31.9, 25.9, 21.4, 19.6, 18.3
24. J.S. Hubbard, and T.M. Harris J. Org. Chem. 46 1981 2566 2570