Highly efficient intra-and intermolecular [4 + 2] cycloaddition reaction catalyzed by rhodium complex

Organic Letters

Volumn 1, Issue 13, 1999, Pages 2045-2047

  Paik, Se Jung ^a   Son, Seung Uk ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000257154     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990169l     Document Type: Article

References (30)

1. For reviews on Diels-Alder reaction, see: (a) Danishefsky, S. Aldrichimica Acta 1986, 19, 59.
2. (b) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5. p 315.
3. (c) Kagan, H.; Riant, O. Chem. Rev. 1992, 92, 1007.
4. (d) Pindur, U.; Lutz, G.; Otto, C. Chem. Rev. 1993, 93, 741.
5. (e) Delox, L.; Srebnik, M. Chem. Rev. 1993, 93, 763.
6. (f) Togni, A.; Venanzi, L. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 497.
7. (g) Fringuelli, F.; Tatichi, A. Dienes in the Diels-Alder Reaction; Wiley: New York, 1990.
8. (h) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990.
9. (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1966, 5, 211.
10. (b) Ciganik, E. Org. React. 1984, 32, 1.
11. (c) Fallis, A. G. Can. J. Chem. 1984, 62, 183.
12. (d) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248.
13. For intramolecular [4 + 2] cycloaddition reactions, see: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432.
14. (b) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965.
15. (c) Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824.
16. (d) McKinstry, L. Livinghouse, T. Tetrahedron 1994, 50, 6145.
17. (e) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
18. (f) Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075.
19. (g) Gilbertson, S. R.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077.
20. (h) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047.
21. For intermolecular [4 + 2] cycloaddition reactions, see: (i) tom Dieck, H.; Diercks, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 778.
22. (j) Mach, K.; Antropiusová, H.; Petrusová, L.; Turecek, F.; Hanus, V. J. Organomet. Chem. 1985, 289, 331.
23. (k) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361.
24. Son, S. U.; Paik, S.-J.; Chung, Y. K. J. Mol. Catal. In press.
25. Scotti, M.; Valderrama, M.; Ganz, R.; Werner, H. J. Organomet. Chem. 1985, 286, 399.
26. +): calcd 293.0776, obsd 293.0741.
27. (a) Jonas, K. Pure Appl. Chem. 1990, 62, 1169.
28. (b) Kündig, E. P.; Jeger, P.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2161.
29. (a) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443.
30. (b) Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253.