TADDOL-TiCl2 catalyzed Diels-Alder reactions: Unexpected influence of the substituents in the 2-position of the dioxolane ring on the stereoselectivity

Tetrahedron Asymmetry

Volumn 8, Issue 15, 1997, Pages 2561-2570

  Altava, Belén ^a   Burguete, Ma Isabel ^a   Fraile, José M ^b   García, José I ^b   Luis, Santiago V ^a   Mayoral, José A ^b   Royo, Ana J ^b   Vicent, María J ^a  

^a UNIVERSITAT JAUME I   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030871439     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00264-4     Document Type: Article

References (26)

1. Seebach, D; Weidmann, B.; Wilder, L. in "Modern Synthetic Methods", Scheffold, R., Ed., Wiley, New York, 1983, vol. 3, p.217.
2. Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
3. (a) Narasaka, K.; Inoue, M.; Ojeda, N. Chem. Lett. 1989, 1109.
4. (b) Narasaka, K.; Inoue, M.; Yamada, T. Chem. Lett. 1986, 1967.
5. (c) Narasaka, K.; Inoue, M.; Yamada, T.; Sugimori, J.; Iwasawa, N. Chem. Lett. 1987, 2409.
6. (d) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340.
7. (e) Narasaka, K.; Inoue, M.; Sugimori, J.; Kawase, Y. Chem. Lett. 1989, 1947.
8. (f) Narasaka, K.; Saitou, M.; Iwasawa, N. Tetrahedron: Asymmetry 1991, 2, 643.
9. (g) Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743.
10. (h) Engler, T. A.; Letavic, M. A.; Takugasawa, F. Tetrahedron Lett. 1992, 33, 6731.
11. (i) Posner, G. H.; Carry, J.-C.; Lee, J. K.; Bull, D. S.; Dai, H. Tetrahedron Lett. 1994, 35, 1321.
12. Corey, E. J.; Matsumura, Y. Tetrahedron Lett. 1991, 32, 6289.
13. (a) Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581.
14. (b) Narasaka, K.; Tanaka, H.; Kanai, F. Bull. Chem. Soc. Jpn. 1991, 64, 387.
15. Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
16. Haase, C.; Sarko, C. R.; DiMare, M. J. Org. Chem. 1995, 60, 1777.
17. (a) Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1995, 777, 4435.
18. (b) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 6487.
19. Seebach, D.; Marti, R. E.; Hintermann, T. Helv. Chim. Acta 1996, 79, 1710.
20. Altava, B.; Burguete, M. I.; Escuder, B.; Luis, S. V.; Salvador, R. V.; Fraile, J. M.; Mayoral, J. A.; Royo, A. J. J. Org. Chem., 1997, 62, 3126.
21. Gothelf, K. V.; Jørgensen, K. A. J. Chem. Soc., Perkin Trans. 2 1997, 111.
22. Seeman, J. I. Chem. Rev. 1983, 83, 83.
23. (a) Allinger, N. L. J. Am. Chem. Soc. 1977, 99 8127.
24. (b) Burkert, U.; Allinger, N. L. "Molecular Mechanics", American Chemical Society, Washington D.C., 1982.
25. Irurre, J.; Alonso-Alija, C.; Piniella, J. F.; Alvárez-Larena, A. Tetrahedron: Asymmetry 1992, 3, 1591.
26. CS Chem3D Pro™, Version 3.5.1. CambridgeSoft Corporation (1996).