Lanthanide catalysts for the hetero Diels-Alder reaction: Effect of ligand structure and acidity

Canadian Journal of Chemistry

Volumn 75, Issue 8, 1997, Pages 1047-1054

  Spino, Claude ^a   Clouston, Laurel L ^b   Berg, David J ^b  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b UNIVERSITY OF VICTORIA   (Canada)

Author keywords

Catalyst; Hetero Diels Alder; Lanthanide; Lanthanum; Ytterbium; Yttrium

Indexed keywords

ALDEHYDES; CATALYST ACTIVITY; ETHERS; LANTHANUM COMPOUNDS; MOLECULAR STRUCTURE; PH EFFECTS; YTTERBIUM COMPOUNDS; YTTRIUM COMPOUNDS;

CROTONALDEHYDE; DIELS ALDER REACTION; ETHYL VINYL ETHER; LIGANDS;

CATALYSTS;

EID: 0031213456     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-125     Document Type: Article

References (45)

1. (a) D.L. Bogerand S. Weinreb. In Hetero Diels-Alder methodology in organic synthesis. Academic Press, San Diego, Calif. 1987;
2. (b) W. Carruthers. In Cycloaddition reactions in organic synthesis. Pergamon Press, Exeter, U.K. 1990.
3. T.L.B. Boivin. Tetrahedron, 43, 3309 (1987), and refs. therein.
4. S. Danishefsky, N. Kato, D. Askin, and J.F. Kerwin, Jr. J. Am. Chem. Soc. 104, 360 (1982); S. Danishefsky and J.F. Kerwin, Jr. J. Am. Chem. Soc. 104, 3183 (1982), and refs. therein.
5. S. Danishefsky, N. Kato, D. Askin, and J.F. Kerwin, Jr. J. Am. Chem. Soc. 104, 360 (1982); S. Danishefsky and J.F. Kerwin, Jr. J. Am. Chem. Soc. 104, 3183 (1982), and refs. therein.
6. J.W. Westley. In Polyether antibiotics: naturally occurring acid ionophores. Vols. I and II. Edited by J.W. Westley. Marcel Dekker, Inc., New York. 1982.
7. (a) H.B. Kagan and J.L. Namy. Tetrahedron, 42, 6573 (1986);
8. (b) G.A. Molander. Chem. Rev. 92, 29 (1992);
9. (c) T. Imamoto. In Lanthanides in organic synthesis. Academic Press, San Diego, Calif. 1994.
10. (a) S. Danishefsky and M. Bednarski. Tetrahedron Lett. 25, 721 (1984);
11. (b) M. Bednarski and S. Danishefsky. J. Am. Chem. Soc. 105, 6968 (1983).
12. R.I. Longley, Jr. and W.S. Emerson. J. Am. Chem. Soc. 72, 3079 (1950).
13. (a) W.G. Dauben and H.D. Krabbenhoft. J. Org. Chem. 42, 282 (1977);
14. (b) B.B. Snider and G.B. Phillips. J. Org. Chem. 48, 2790 (1983).
15. C. Spino, G. Liu, N. Tu, and S. Girard. J. Org. Chem. 59, 5596 (1994).
16. T. Oh and M. Reilly. Org. Prep. Proced. Int. 26, 129 (1994), and refs. cited therein.
17. (a) M. Bednarski, C. Maring, and S. Danishefsky. Tetrahedron Lett. 24, 3451 (1983);
18. (b) M. Bednarski and S. Danishefsky. J. Am. Chem. Soc. 108, 7060 (1986).
19. C. Spino, L. Clouston, and D. Berg. Can. J. Chem. 74, 1762 (1996).
20. M.L. Morris and R.D. Koob. Org. Mass Spectrom. 17, 503 (1982).
21. A. Smith, S.J. Rettig, and C. Orvig. Inorg. Chem. 27, 3929 (1988).
22. P. Shao, D.J. Berg, and G.W. Bushnell. Inorg. Chem. 33, 3452 (1994).
23. A.H. Cowley, N.C. Norman, and M. Pakulski. Inorg. Synth. 27, 235 (1990).
24. S.R. Ditto, R.J. Card, P.D. Davis, and D.C. Neckers. J. Org. Chem. 44, 394 (1979).
25. F. Vögtle, M. Zuber, and R.G. Lictenthaler. Chem. Ber. 106, 717 (1973).
26. S.N. Huckin and L. Weiler. J. Am. Chem. Soc. 96, 1082 (1974).
27. D.C. Bradley, J.S. Ghotra, and F.A. Hart. J. Chem. Soc. Dalton Trans. 1021 (1973).
28. D.J. Berg, S.J. Rettig, and C. Orvig. J. Am. Chem. Soc. 113, 2528 (1991).
29. R.C. Mehrotra, R. Bohra, and D.P. Gaur. In Metal β-diketonates and allied derivatives. Academic Press, New York. 1978.
30. (a) E.H. Barash, P.S. Coadn, E.B. Lobkovsky, W.E. Streib, and K.G. Caulton. Inorg. Chem. 32, 497 (1993).
31. (a) M. Nakamura, R. Nakamura, K. Nagai, M. Shimoi, S. Tomoda, Y. Takeuchi, and A. Ouchi. Bull. Chem. Soc. Jpn. 59, 332 (1986);
32. (b) A.T. McPhail, P.S.W. Tschang, and P.M. Gross, J. Chem. Soc. Dalton Trans. 1165 (1974);
33. (c) R.A. Lalancette, M. Cefola, W.C. Hamilton, and S.J. La Placa. Inorg. Chem. 6, 2127 (1967);
34. (d) J.G. Leipoldt, L.D.C. Bok, S.S. Basson, A.E. Laubscher, and J.S. van Vollenhoven. J. Inorg. Nucl. Chem. 39, 301 (1977).
35. M.J. Bennett, F.A. Cotton, P. Legzdins, and S.J. Lippard. Inorg. Chem. 7, 1770 (1968).
36. R.F. Childs, D.L. Mullholland, and A. Nixon. Can. J. Chem. 60, 801 (1982).
37. (a) E.P. Serjeant and B. Dempsey. In IUPAC: Ionisation constants of organic acids in aqueous solution. Pergamon Press, Toronto. 1979;
38. (b) R.L. Lintvedt and H.F. Hotzclow. Inorg. Chem. 5, 239 (1966);
39. (c) B.B. Martin and D.F.J. Martin. Inorg. Nucl. Chem. 41, 1503 (1979);
40. (d) R.W. Green and E.L. LeMesurier. Aust. J. Chem. 19, 229 (1966);
41. (e) J. Betts and J. Barclay. Can. J. Chem. 33, 1768 (1955);
42. (f) P.D. Maria, A. Fontana, D. Spinelli, C. Dell'Erba, and M. Novi. J. Chem. Soc. Perkin Trans. 2, 4, 649 (1993).
43. (a) P. Laszlo and M. Teston. J. Am. Chem. Soc. 112, 8750 (1990);
44. (b) P.V. Bonnesen, G.L. Puckett, R.V. Honeychuck, and W.H. Hersh. J. Am. Chem. Soc. 111, 6070 (1989).
45. M.F. Lappert, A. Singh, and R.G. Smith. Inorg. Synth. 27, 164 (1990).