Hetero Diels-Alder reactions catalyzed by the metallocenium complex [Cp*2Ce][BPh4]

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 1215-1217

  Molander, Gary A ^a   Rzasa, Robert M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LANTHANIDE;

ACIDITY; ARTICLE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

BENZALDEHYDES; CATALYSIS; LANTHANUM; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS; PYRONES;

EID: 0034712304     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9909195     Document Type: Article

References (51)

1. Bach, T.; Fox, D. N. A.; Reetz, M. T. J. Chem. Soc., Chem. Commun. 1992, 1634.
2. Jordan, R. F.; Dasher, W. E.; Echols, S. F. J. Am. Chem. Soc. 1986, 108, 1718.
3. (a) Wipf, P.; Xu, W. Tetrahedron 1995, 51, 4551.
4. (b) Collins, S.; Koene, B. E.; Ramachandran, R.; Taylor, N. J. Organometallics 1991, 10, 2092.
5. (c) For an asymmetric cationic catalyst, see: Hong, Y.; Kuntz, B. A.; Collins, S. Organometallics 1993, 12, 964.
6. Kundig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 1220.
7. Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y. J. Org. Chem. 1999, 64, 8660.
8. (a) Hazin, P. N.; Bruno, J. W.; Schulte, G. K. Organometallics 1990, 9, 416.
9. (b) Evans, W. J.; Ulibarri, T. A.; Chamberlain, L. R.; Alvarez, J. W., Jr. Organometallics 1990, 9, 2124.
10. (c) Heeres, H. J.; Meetsma, A.; Teuben, J. H. J. Organomet. Chem. 1991, 414, 351.
11. (d) Schaverien, C. J. Organometallics 1992, 11, 3476.
12. (e) Deng, D.; Zheng, X.; Qian, C.; Sun, J.; Dormand, A.; Baudry, D.; Visseaux, M. J. Chem. Soc., Dalton Trans. 1994, 1665.
13. (f) Schumann, H.; Winterfeld, J.; Keitsch, M. R.; Herrmann, K.; Demtschuk, J. Z. Anorg. Allg. Chem. 1996, 622, 1457.
14. (g) Yuan, F.; Shen, Q.; Sun, J. J. Organomet. Chem. 1997, 538, 241.
15. (h) Evans, W. J.; Seibel, C. A.; Ziller, J. W. J. Am. Chem. Soc. 1998, 120, 6745.
16. (i) Cendrowski-Guillaume, S. M.; Nierlich, M.; Lance, M.; Ephritikhine, M. Organometallics 1998, 17, 786.
17. (j) Song, X.; Thornton-Pett, M.; Bochmann, M. Organometallics 1998, 17, 1004.
18. (a) Evans, W. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; John Wiley & Sons: Chichester, 1982.
19. (b) Schumann, H.; Genthe, W. In Handbook on the Chemistry and Physics of Rare Earths; Gschneidner, K. A., Jr., Eyring, L., Eds.; Elsevier: Amsterdam, 1984.
20. (c) Schumann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 474.
21. (d) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 131.
22. (e) Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982; Vol. 3.
23. (f) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
24. (g) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283.
25. (h) Metallocenes; Togni, A., Halterman, R. L., Eds.; Wiley-VCH: Weinheim, 1998.
26. (a) Strauss, S. H. Chem. Rev. 1993, 93, 927.
27. (b) Chen, Y.-X.; Stern, C. L.; Yang, S.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 12451.
28. (c) Jia, L.; Yang, X.; Stern, C. L.; Marks, T. J. Organometallics 1997, 16, 842.
29. (d) Li, L.; Marks, T. J. Organometallics 1998, 17, 7, 3996.
30. (e) Chen, Y.-X.; Metz, M. V.; Li, L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 6287.
31. (f) Lanza, G.; Fragalà, I. L.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 8257.
32. (g) Luo, L.; Marks, T. J. Top. Catal. 1999, 7, 97.
33. (a) Danishefsky, A.; Kerwin, J. F., Jr.; Kobayashi, S. J. Am. Chem. Soc. 1982, 104, 358.
34. (b) Danishefsky, A.; Kerwin, J. F., Jr. J. Org. Chem. 1982, 47, 3183.
35. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1986, 108, 7060.
36. (a) Tietze, L. F.; Kettschau, G. Top. Curr. Chem. 1997, 189, 1.
37. (b) Danishefsky, S. J. Chemtracts-Org. Chem. 1989, 2, 273.
38. (c) Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis; Academic Press: New York, 1987; p 94.
39. (d) Schaus, S. E.; Brenalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 4876.
40. (e) Ghosh, A. K.; Mathivanan, P.; Cappiello, J. Tetrahedron Lett. 1997, 38, 2427.
41. Van de Weghe, P.; Collin, J. Tetrahedron Lett. 1994, 35, 2545.
42. (a) Schaus S. E.; Branalt, J.; Jacobsen E. N. J. Org. Chem. 1998, 63, 403.
43. (b) Hanamoto, T.; Furuno, H.; Sugimoto, Y.; Inanaga, J. Synlett 1997, 79.
44. (c) Ghosh, A. K.; Mathivanan, P.; Cappiello, J.; Krishnan, K. Tetrahedron Asymmetry 1996, 7, 2165.
45. (d) Keck, G. E.; Li, X.-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
46. (e) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907.
47. Gerstberger, G.; Palm, C.; Anwander, R. Chem. Eur. J. 1999, 5, 997.
48. 3 as solvent see: Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716.
49. Bosnich, B. Aldrichim. Acta 1998, 31, 76.
50. Larson, E. R.; Danishefsky, S. Tetrahedron Lett. 1982, 23, 1975.
51. Sher, F.; Isidor, J. L.; Taneja, H. R.; Arlson, R. M. Tetrahedron Lett. 1973, 8, 577.