Diastereoselective Diels-Alder reaction of 5-(indol-2-yl)- pyran-2-one

Tetrahedron

Volumn 56, Issue 29, 2000, Pages 5205-5208

  Passarella, Daniele ^a   Lesma, Giordano ^a   Martinelli, Marisa ^a   Silvani, Alessandra ^a   Cantò, Margalida ^b   Hidalgo, Josè ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Cycloaddition; Indoles; Lanthanides; Pyrones

Indexed keywords

2 PYRONE DERIVATIVE; AMINE;

ARTICLE; CATALYST; CHEMICAL REACTION; GEL CHROMATOGRAPHY; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0034647708     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00183-6     Document Type: Article

References (26)

1. For a review see: Afarinkia, K.; Vinader, M. V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111.
2. For diastereoselective Diels-Alder reactions of substituted 2-pyrones see: (a) Afarinkia, K.; Posner, G. H. Tetrahedron Lett. 1992, 33, 7839.
3. (b) Shimo, T.; Kataoka, K.; Maeda, A.; Somekawa, K. J. Het. Chem. 1992, 29, 811.
4. (c) Posner, G. H.; Nelson, T. D.; Kinter, C. M.; Johnson, N. J. Org. Chem. 1992, 57, 4083.
5. (d) Marko, I. E.; Evans, G. R. Synlett 1994, 431.
6. (e) Posner, G. H.; Carry, J.-C.; Lee, J. K.; Bull, D. S.; Dai, H. Tetrahedron Lett. 1994, 35, 1321.
7. (f) Marko, I. E.; Evans, G. R. Tetarahedron Lett. 1994, 35, 2767.
8. (g) Posner, G. H.; Hutchings, R. H.; Woodard, B. T. Synlett 1997, 432.
9. (h) Afarinkia, K.; Daly, N. T.; Gomez-Farnos, S.; Joshi, S. Tetrahedron Lett. 1997, 38, 2369.
10. (i) For reactivity of 2-pyrones with benzyne see: Escudero, S.; Perez, D.; Guitian, E.; Castedo, L. Tetrahedron Lett. 1997, 38, 5375.
11. For enantioselective Diels-Alder reactions of substituted 2-pyrones D.-A. reactions see: (a) Marko, I. E.; Evans, G. R. Tetatrahedron Lett. 1994, 35, 2771.
12. (b) Marko, I. E.; Evans, G. R.; Seres, P.; Chelle, I.; Janousek, Z. Pure & Appl. Chem. 1996, 68, 113.
13. (c) Posner, G. H.; Dai, H.; Scott Bull, D.; Lee, J.-K.; Eydoux, F.; Ishiharad, Y.; Welsh, W.; Pryor, N.; Petr, Jr., S. J. Org. Chem. 1996, 61, 671.
14. (d) Marko, I. E.; Evans, G. R.; Seres, P.; Chellè-Regnaut, I.; Leroy, B.; Warriner, S. L. Tetrahedron Lett. 1997, 38, 4269.
15. (e) Okamura, H.; Morishige, K.; Iwagawa, T.; Nakatani, M. Tetrahedron Lett. 1998, 39, 1211.
16. (f) Coelho, P.; Blanco, L. Tetrahedron Lett. 1998, 39, 4261.
17. (a) Posner, G. H.; Carry, J.-C.; Anjeh, T. E. N.; French, A. N. J. Org. Chem. 1992, 57, 7012.
18. (b) Posner, G. H.; Eydoux, F.; Lee, J. K.; Bull, D. S. Tetrahedron Lett. 1994, 35, 7541.
19. (c) Afarinkia, K.; Mahmood, F. Tetrahedron Lett. 1998, 39, 7413.
20. (d) Afarinkia, K.; Mahmood, F. Tetrahedron 1999, 55, 3129.
21. (e) Kusama, H.; Mori, T.; Mitani, I.; Kashima, H.; Kuwajima, I. Tetrahedron Lett. 1997, 38, 4129.
22. Danieli B., Lesma G., Martinelli M., Passarella D., Peretto I., Silvani A. Tetrahedron. 54:1998;14081.
23. +).
24. For other examples of lanthanide catalysis of substituted 2-pyrones see: (a) Marko, I. E.; Evans, G. R. Tetarahedron Lett. 1994, 35, 2767.
25. (b) Marko, I. E.; Evans, G. R. Synlett 1994, 431. See also Refs. 3a,b,d,4e.
26. Burgstahler W.W., Gibbson L.K., Nordin I.C. J. Chem. Soc. 24:1963;4986.