Silver(I)-catalyzed addition of zirconocenes to epoxy esters: A new entry to 1,4-dicarbonyl compounds and pyridazinones

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1253-1255

  Wipf, Peter ^a   Methot, Joey Lee ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000419893     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990924v     Document Type: Article

References (28)

1. Coates, W. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Exeter, U.K., 1996; Vol. 6, pp 1-91.
2. See, for example: (a) Tisler, M.; Stanovnik, B. Adv. Heterocycl. Chem. 1990, 49, 385.
3. (b) Kuroda, S.; Akahane, A.; Itani, H.; Nishimura, S.; Durkin, K.; Kinoshita, T.; Tenda, Y.; Sakane, K. Bioorg. Med. Chem. Lett. 1999, 9, 1979.
4. (a) Wipf, P.; Xu, W.; Takahashi, H.; Jahn, H.; Coish, P. D. G. Pure Appl. Chem. 1997, 69, 639.
5. (b) Wipf, P.; Takahashi, H.; Zhuang, N. Pure Appl. Chem. 1998, 70, 1077.
6. (c) Wipf, P.; Tsuchimoto, T.; Takahashi, H. Pure Appl. Chem. 1999, 71, 415.
7. (a) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 825.
8. (b) Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 5880.
9. (c) Wipf, P.; Xu, W.; Kim, H.; Takahashi, H. Tetrahedron 1997, 53, 16575.
10. (d) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
11. (e) Suzuki, K. Pure Appl. Chem. 1994, 66, 1557.
12. 13C NMR, IR, MS, and HR-MS. Copies of NMR spectra are included in the Supporting Information.
13. (a) Buchwald, S. L.; La Maire, S. J.; Nielson, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
14. (b) Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
15. 4 adsorbed onto Celite from an aqueous solution and dried in vacuo.
16. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1985, 26, 6015.
17. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
18. Csende, F.; Szabo, Z.; Bernath, G. Synthesis 1995, 1240.
19. Nefzi, A.; Ostresh, J. M.; Houghton, R. A. Chem. Rev. 1997, 97, 449.
20. (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823.
21. (b) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
22. (c) Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 4649.
23. (d) Wipf, P.; Reeves. J. T. Tetrahedron Lett. 1999, 40, 5139.
24. (e) Röver, S.; Wipf, P. Tetrahedron Lett. 1999, 40, 5667.
25. For a pioneering solid support version of this strategy, see: Camps, F.; Cartells, J.; Pi, J. An. Quim. 1974, 70, 848. Review: Obrecht, D.; Villalgordo, J. M. Solid-supported combinatorial and parallel synthesis of small-molecular weight compound libraries: Pergamon: Oxford, 1998.
26. For a pioneering solid support version of this strategy, see: Camps, F.; Cartells, J.; Pi, J. An. Quim. 1974, 70, 848. Review: Obrecht, D.; Villalgordo, J. M. Solid-supported combinatorial and parallel synthesis of small-molecular weight compound libraries: Pergamon: Oxford, 1998.
27. 3 to a cold (-75°C) solution of fumaryl chloride and β-methallyl alcohol, followed by hydrolysis.
28. 14 isomers (bp 56°C). It is immiscible with most common organic solvents.