A new chiral ligand for the Fe-Lewis acid catalysed asymmetric Diels-Alder reaction

Chemical Communications

Volumn , Issue 23, 1998, Pages 2635-2636

  Bruin, Marion E ^a   Peter Kundig E ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; LIGAND;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; SYNTHESIS;

EID: 0032494979     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a806445h     Document Type: Article

References (22)

1. For recent reviews, see: K. Narasaka, Synthesis, 1991, 1;
2. H. B. Kagan and O. Riant, Chem. Rev., 1992, 92, 1007;
3. U. Pindur, G. Lutz and C. Otto, Chem. Rev., 1993, 93, 741;
4. E. J. Corey and A. Guzman-Perez, Angew. Chem. Int. Ed. Engl., 1998, 37, 389.
5. For asymmetric Diels-Alder reactions catalysed by chiral Cp- and arene-transition metal Lewis acids, see: (a) E. P. Kündig, B. Bourdin and G. Bemardinelli, Angew. Chem., Int. Ed. Engl., 1994, 33, 1856;
6. (b) D. Carmona, C. Cativiela, R. García-Correas, F. J. Lahoz, M. P. Lamata, J. A. López, M. P. López-Ram de Víu, L. A. Oro, E. San José and F. Viguri, Chem. Commun., 1996, 1247;
7. (c) D. L. Davies, J. Fawcett, S. A. Garratt and D. R. Russell, Chem. Commun., 1997, 1351;
8. (d) D. Carmona, C. Cativiela, S. Elipe, F. J. Lahoz, M. P. Lamata, M. P. López-Ram de Víu, L. A. Oro, C. Vega and F. Viguri, Chem. Commun., 1997, 2351;
9. (e) A. J. Davenport, D. L. Davies, J. Fawcett, S. A. Garratt, L. Lad and D. R. Russell, Chem. Commun., 1997, 2347.
10. (a) E. P. Kündig, C. Dupré, B. Bourdin, A. Cunningham Jr. and D. Pons, Helv. Chim. Acta, 1994, 77, 421;
11. (b) A. F. Cunningham Jr. and E. P. Kündig, J. Org. Chem., 1988, 53, 1823.
12. R. Seemayer and M. P. Schneider, J. Chem. Soc., Chem. Commun., 1991, 49.
13. K. B. Sharpless, W. Amberg, Y. L. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeone, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768;
14. Z.-M. Wang and K. B. Sharpless, J. Org. Chem., 1994, 59, 8302.
15. M. Kawashima and R. Hirata, Kankyo Kagaku Sentaa Kk. Jpn. Kokai Tokkyo Koho JP, 66,345,789, 1994.
16. Chem. Abstr., 1995, 123, 33385r.
17. M. Fild, O. Glemser and I. Hollenberg, Z. Naturforsch Teil B, 1966, 21, 920;
18. R. Ali and K. B. Dillon, J. Chem. Soc., Dalton Trans., 1990, 2593.
19. K. Furuta, S. Shimizu, Y. Miwa and H. Yamamoto, J. Org. Chem., 1989, 54, 1481.
20. S. Hashimoto, N. Komeshima and K. Koga, J. Chem. Soc., Chem. Commun., 1979, 437.
21. E. J. Corey and T.-P. Loh, J. Am. Chem. Soc., 1991, 113, 8966;
22. L. A. Paquette, C. W. Doecke, F. R. Kearney, A. F. Drake and S. F. Mason, J. Am. Chem. Soc., 1980, 102, 7228.