Catalytic, enantioselective, inverse electron-demand Diels-Alder reactions of 2-pyrone derivatives

Pure and Applied Chemistry

Volumn 68, Issue 1, 1996, Pages 113-122

  Markó, István E ^a   Evans, Graham R ^a   Seres, Peter ^a   Chellé, Isabelle ^a   Janousek, Zdenek ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002126695     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668010113     Document Type: Article

References (47)

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2. b. Markó, I. E. Organometallic Reagents in Orgenic Synthesis, Chapter 2, p 44-56, Academic Press Ltd., 1994.
3. c. Markó, I. E.; Evans, G. R.; Seres, P.; Swarbrick, T. M.; Kennard, L.; Declercq, J.-P.; Tinant, B.; Feneau-Dupont, J. Acros Organics Acta, 1995, 1, 26.
4. a. For an early example of this methodology, see: Krantz, A., Lin, C. J. Am. Chem. Soc., 1973, 95, 5662.
5. b.For the use of 5-carbomethoxy-2-pyrone in the same methodology, see: Eto, M.; Harano, K.; Hisano, T., J. Chem. Soc. Perkin II, 1993, 963.
6. For an excellent monograph on tandem reactions, see: Ho, T. L. Tandem Organic Reactions, 1992, J. Wiley & Sons, New York.
7. a. Markó, I. E.; Seres, P.; Evans, G. R.; Swarbrick, T. M., Tetrahedron Lett., 1993, 34, 7305.
8. b. Markó, I. E., Seres, P., Swarbrick, T. M., Staton, I., Adams, H., Tetrahedron Lett., 1992, 33, 5649. For other relevant work in this area, see: references 7a-d.
9. For reviews on pyrones, see: a. Kvita, V.; Fischer, W., Chimia, 1993, 47, 3.
10. b. Kvita, V.; Fischer, W., Chimia, 1992, 46, 457.
11. c. Posner, G. H.; Afarinkia, K.; Vinader, V.; Nelson, T. O.,Tetrahedron, 1992, 48, 9111.
12. d. Shusherina, N. P., Russ. Chem. Rev., 1974, 43, 851.
13. Mander, L. N. Chem. Rev., 1992, 92, 573.
14. For extensive use of other electron-deficient 2-pyrone derivatives, see: a. 3-sulphinyl-2-pyrone, Posner, G. H.; Haces, A.; Harrison, W.; Kinter, C. M. J. Org. Chem., 1987, 52, 4836.
15. b. 3-sulphonyl-2-pyrone, Posner, G. H., Kinter, C. M. J. Org. Chem., 1990, 55, 3967.
16. c. 3-bromo-2-pyrone, Susherina, N. P.; Nesterova, T. L.; Polyakova, O. V. J. Org. Chem. USSR, 1980, 16, 1111. (See also: Posner, G. H.; Nelson, T. D.; Kinter, C. M.; Afarinkia, K. Tetrahedron Lett., 1991, 32, 5295).
17. c. 3-bromo-2-pyrone, Susherina, N. P.; Nesterova, T. L.; Polyakova, O. V. J. Org. Chem. USSR, 1980, 16, 1111. (See also: Posner, G. H.; Nelson, T. D.; Kinter, C. M.; Afarinkia, K. Tetrahedron Lett., 1991, 32, 5295).
18. d. 5-bromo-2-pyrone, Afarinkia, K.; Posner, G. H. Tetrahedron Lett., 1992, 33, 7839.
19. For the cycloaddition reactions of 5-carbomethoxy-2-pyrone (5-CMP) with enol ethers, see : e. Shimo, T.; Iwakiri, T.; Somekawa, K., J. Heterocyclic Chem., 1992, 29, 199 and references cited therein. We are grateful to Prof. Shimo for sending us preprints of his work.
20. Posner, G. H. Pure and Appl. Chem. 1990, 62, 1949.
21. Markó, I. E.; Evans, G. R,Tetrahedron Lett., 1993, 34, 7309.
22. Markó, I. E., Evans, G. R. Synlett., 1994, 431.
23. The usual Lewis acids are too powerful to catalyse this reaction. We have found that either polymerisation of the vinyl ether component or formation of the pyrilium salt of the 2-pyrone took place. In all cases, little or no cycloaddition was observed. It is also noteworthy that decarboxylation of the bicyclic lactones occured readily with almost any common Lewis acids.
24. a. Posner, G. H., Wettlaufer, D. G. Tetrahedron Lett., 1986, 27, 667.
25. b. Posner, G. H., Kinter, C. M. J. Org. Chem., 1990, 55, 3967.
26. Thornton, E., Prapansiri, V. Tetrahedron Lett., 1991, 32, 3147.
27. a. Markó, I. E.; Evans, G. R.; Declercq, J.-P. Tetrahedron, 1994, 50, 4557.
28. b. Markó, I. E.; Evans, G. R Tetrahedron Lett., 1994, 35, 2767.
29. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R., Angew. Chem. Int. Ed. Engl., 1985, 24, 1.
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31. a. Helmchen, G.; Karge, R.; Weetman, J. Modern Synthetic Methods, 1986; Scheffold, R., Ed.; Springer: Heidelberg, 1986; Vol. 4, p 262.
32. b. Heimchen, G.; Abdel Hady, A. F.; Hartman, H.; Karge, R.; Krotz, A.; Sartor, K.; Urmann, M., Pure Appl. Chem., 1989, 62, 409.
33. The group of Posner has also recently reported the diastereocontrolled IEDDA cycloaddition of benzyl vinyl ether to the methyl lactate ester of 3-CMP appeared: Posner, G. H.; Carry, J.-C.; Anjeh, T. E. N.; French, A. N., J. Org. Chem., 1992, 57, 7012. Our results contrast with those reported in this article and highlight again the increase facial selectivity provided by the pantolactone auxiliary over the lactate. Indeed, using the lactate derived 2-pyrone, careful control of the reaction conditions (temperature, solvent) is required and a significant fall in diastereocontrol is observed when an achiral lanthanide is used or when mismatching with the enantiomeric praesodymium complex occurs.
34. Declercq, J.-P.; Feneau-Dupont, J.; Markó, I. E.; Evans, G. R. Zeitsch. für Krist., 1995, 210, 531.
35. Markó, I. E.; Evans, G. R. unpublished observations.
36. a. Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M., Tetrahedron Lett., 1993, 34, 4535.
37. b. Kobayashi, S.; Hachiya, I.; Takahori, T.; Araki, M.; Ishitani, H. Tetrahedron Lett., 1992, 33, 6815. For an excellent review, see: Kobayashi, S. We are extremely grateful to Professor Kobayashi for sending us preprints of his work.
38. a. Markó, I. E.; Evans, G. R. Tetrahedron Lett., 1994, 35, 2771.
39. b. Markó, I. E.; Evans, G. R.; Declercq, J.-P. Tetrahedron, 1994, 50, 4557.
40. 3 coordinates too strongly to 3-CMP, forming the unreactive pyrillium form. By adding an alcohol, a diol, an aminoalcohol or nitromethane, the Lewis acidity of the lanthanide is lowered and IEDDA reaction ensues.
41. Markó, I. E., Evans, G. R., Declercq, J.-P., Feneau-Dupont, J., Tinant, B. unpublished observations.
42. a. Markó, I. E., Evans, G. R., Declercq, J.-P., Feneau-Dupont, J., Tinant, B. Acros Organics Acta, 1995,1, 63.
43. b. Markó, I. E., Evans, G. R., Declercq, J.-P., Feneau-Dupont, J., Tinant, B. Bull. Soc. Chim. Belg., 1994, 103, 295.
44. The enantioselective IEDDA of 3-CMP with benzyl vinyl ether, promoted by the Narasaka Titanium-Taddol reagent was recently reported: Posner, G. H.; Carry, J.-C.; Lee, J. K.; Bull, D. S.; Dai, H. Tetrahedron Lett., 1994, 35, 1321.
45. A proposed structure for the active lanthanide complex has recently been published: a. Kobayashi, S., Ishitani, H. J. Am. Chem. Soc., 1994, 116, 4083. b. Kobayashi, S. Synlett., 1994, 689. c. Kobayashi, S.; Ishitani, H.; Hachiya, L; Araki, M. Tetrahedron, 1994, 50, 11623. We are grateful to Professor Kobayashi for sending us a preprint of this work.
46. A proposed structure for the active lanthanide complex has recently been published: a. Kobayashi, S., Ishitani, H. J. Am. Chem. Soc., 1994, 116, 4083. b. Kobayashi, S. Synlett., 1994, 689. c. Kobayashi, S.; Ishitani, H.; Hachiya, L; Araki, M. Tetrahedron, 1994, 50, 11623. We are grateful to Professor Kobayashi for sending us a preprint of this work.
47. A proposed structure for the active lanthanide complex has recently been published: a. Kobayashi, S., Ishitani, H. J. Am. Chem. Soc., 1994, 116, 4083. b. Kobayashi, S. Synlett., 1994, 689. c. Kobayashi, S.; Ishitani, H.; Hachiya, L; Araki, M. Tetrahedron, 1994, 50, 11623. We are grateful to Professor Kobayashi for sending us a preprint of this work.