Use of FeCl3 and FeCl3 adsorbed on silica as efficient Lewis acid catalyst in ionic Diels-Alder reactions of α,β-unsaturated acetals

Synlett

Volumn , Issue 5, 2001, Pages 667-669

  Chavan, Subhash P ^a   Sharma, Anil K ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Acetals; Diels Alder reactions; Lewis acids; Regioselectivity; Stereoselectivity

Indexed keywords

ACETAL DERIVATIVE; FERRIC CHLORIDE; SILICON DIOXIDE;

ARTICLE; CATALYST; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035036564     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13375     Document Type: Article

References (25)

1. Gassman, P. G.; Singleton, D. A. J. Am. Chem. Soc, 1984, 106, 6085.
2. Gassman, P. G.; Singleton, D. A.; Wilwerding, J. J.; Chavan, S. P. J. Am. Chem. Soc. 1987, 109, 2182.
3. Gassman, P. G.; Chavan, S. P. J. Chem. Soc., Chem. Commun. 1989, 837.
4. Gassman, P. G.; Chavan, S. P. J. Org. Chem. 1988, 53, 2392.
5. Gassman, P. G.; Chavan, S. P.; Fertel, L. B. Tetrahedron Lett. 1990, 31, 6489.
6. Gassman, P. G.; Chavan, S. P. Tetrahedron Lett. 1989, 29, 3407.
7. Grieco, P. A.; Collins, J. L. Handy, S. T. Synlett 1995, 1155.
8. Samakia, T.; Berliner, M. A. J. Org. Chem. 1994, 59, 6890.
9. Kitagawa, O.; Aoki, K.; Inove, T.; Taguchi, T. Tetrahedron Lett. 1995, 36, 593.
10. Inokuchi, T.; Tanigawa S.; Toru, S. J. Org. Chem. 1990, 55, 3958.
11. a) Vankar, P. S.; Reddy, M. V.; Kumareswaran, R.; Pitre, S. V.; Roy, R.; Vankar, Y. D. Tetrahedron 1999, 55, 1099-1110.
12. b) Reddy, G.; Kumareswaran, R.; Vankar, Y. D. Tetrahedron Lett. 2000, 41, 10333.
13. a) Denmark, S. E.; Klix, R. C. Tetrahedron 1988, 44, 4043.
14. b) Tietze, L. F.; Beifuss, U. Synthesis 1988, 359.
15. c) Snider, B. B.; Roush, D. M. J. Org. Chem. 1979, 49, 4229.
16. d) Mahe, L.; Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 3969.
17. a) Keinan, E.; Mazur, Y. J. Org. Chem. 1978, 43, 1022.
18. b) Kim, K. S.; Song, Y. H.: Lee, B. H.; Hahn, C. S. J. Org. Chem. 1986, 51, 404.
19. c) Fadel, A.; Salaun, J. Tetrahedron 1985, 41, 413.
20. d) Patney, H. K. Tetrahedron Lett. 1991, 2259.
21. e) Jempty, T. C.; Gogins, K, A.; Mazur, Y.; Miller, L. L, J. Org. Chem. 1981, 46, 4545.
22. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
23. -1: 2970, 1681, 1625, 1600, 1496, 1404, 1332, 1145, 1109.
24. 3 (50 mg) in DCM at room temperature. The solvent is removed on a rotary evaporator to achieve homogenous adsorption. Finally, the yellow residue was dried under vacuum (0.1 mm Hg) for 30 min to furnish a yellow powder.
25. -1: 3065, 1630, 1335, 1107, 980, 835.