Coupling of Cyclobutenediones with Fischer Carbene Complexes: A One-Step Synthesis of Cyclopentenediones and/or 5-Alkylidenefuranones via Net Insertion of the Carbene Unit into a C - C Bond

Organometallics

Volumn 18, Issue 21, 1999, Pages 4429-4436

  Zora, Metin ^a,b   Li, Yuhui ^a   Herndon, James W ^a,c  

^a Bldg 142   (United States)

^b MIDDLE EAST TECHNICAL UNIVERSITY   (Turkey)

^c NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000388120     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9905198     Document Type: Article

References (35)

1. For a preliminary account of this work, see: Zora, M.; Herndon, J. W. Organometallics 1993, 12, 248-249.
2. Numerous reviews of the use of Fischer carbene complexes in organic synthesis have appeared; the most recent include: (a) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187-198. (b) Wulff, W. D. Organometallics 1998, 17, 3116-3134. (c) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271-288. (d) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163-242. (e) Hegedus, L. S. Tetrahedron 1997, 53, 4105-4128.
3. Numerous reviews of the use of Fischer carbene complexes in organic synthesis have appeared; the most recent include: (a) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187-198. (b) Wulff, W. D. Organometallics 1998, 17, 3116-3134. (c) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271-288. (d) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163-242. (e) Hegedus, L. S. Tetrahedron 1997, 53, 4105-4128.
4. Numerous reviews of the use of Fischer carbene complexes in organic synthesis have appeared; the most recent include: (a) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187-198. (b) Wulff, W. D. Organometallics 1998, 17, 3116-3134. (c) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271-288. (d) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163-242. (e) Hegedus, L. S. Tetrahedron 1997, 53, 4105-4128.
5. Numerous reviews of the use of Fischer carbene complexes in organic synthesis have appeared; the most recent include: (a) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187-198. (b) Wulff, W. D. Organometallics 1998, 17, 3116-3134. (c) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271-288. (d) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163-242. (e) Hegedus, L. S. Tetrahedron 1997, 53, 4105-4128.
6. Numerous reviews of the use of Fischer carbene complexes in organic synthesis have appeared; the most recent include: (a) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187-198. (b) Wulff, W. D. Organometallics 1998, 17, 3116-3134. (c) Harvey, D. F.; Sigano, D. M. Chem. Rev. 1996, 96, 271-288. (d) Aumann, R.; Nienaber, H. Adv. Organomet. Chem. 1997, 41, 163-242. (e) Hegedus, L. S. Tetrahedron 1997, 53, 4105-4128.
7. For the most recent paper focusing on Fischer carbene cyclopropanations, see: Barluenga, J.; Fernandez-Acebes, A.; Trabanco, A. A.; Florez, J. J. Am. Chem. Soc. 1997, 119, 7591-7592.
8. See: Sierra, M. A.; Macheño, M. J.; Sáez, E.; del Amo, J. C. J. Am. Chem. Soc. 1998, 120, 6812-6813, and references therein.
9. For recent examples, see: (a) Mak, C. C.; Tse, M. K.; Chan, K. S. J. Org. Chem. 1994, 59, 3585-3589. (b) Merlic, C. A.; Albaneze, J. Tetrahedron Lett. 1995, 36, 1007-1110.
10. For recent examples, see: (a) Mak, C. C.; Tse, M. K.; Chan, K. S. J. Org. Chem. 1994, 59, 3585-3589. (b) Merlic, C. A.; Albaneze, J. Tetrahedron Lett. 1995, 36, 1007-1110.
11. (a) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699-701.
12. (b) Herndon, J. W.; Zhu, Y. Tetrahedron Lett. 1998, 39, 7443-7446.
13. Harvey, D. F.; Neil D. A. Tetrahedron 1993, 49, 2145-2150.
14. Zora, M.; Herndon, J. W. Organometallics 1994, 12, 3370-3374. To our knowledge, this example and ref 1 are the only examples of C - C bond insertion by a discrete transition metal-carbene complex.
15. Deoxgenations using low-valent chromium has precedent, (a) Turner, S. U.; Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1992, 114, 8394-8404. (b) Wulff, W. D.; Kaesler, R. W.; Peterson, G. A.; Tang, P. C. J. Am. Chem. Soc. 1985, 107, 1060-1062.
16. Deoxgenations using low-valent chromium has precedent, (a) Turner, S. U.; Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1992, 114, 8394-8404. (b) Wulff, W. D.; Kaesler, R. W.; Peterson, G. A.; Tang, P. C. J. Am. Chem. Soc. 1985, 107, 1060-1062.
17. For an alternative synthesis of 2-amino-1,3-cyclopentenediones, see: Sun, L. J.; Liebeskind, L. S. J. Org. Chem, 1994, 59, 6856-6858.
18. (a) For interconversion via thermolysis, see: Claisen, L.; Ewan, T. Justus Liebigs Ann. Chem. 1895, 284, 245-299. (b) For interconversion via base, see: Gedge, D. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1978, 880-882. (c) For utilization of this interconversion for organic synthesis, see: Campbell, A. C.; Maidment, M. S.; Pick, J. H.; Stevenson, D. F. M. J. Chem. Soc., Perkin Trans, 1 1985, 1567-1576.
19. (a) For interconversion via thermolysis, see: Claisen, L.; Ewan, T. Justus Liebigs Ann. Chem. 1895, 284, 245-299. (b) For interconversion via base, see: Gedge, D. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1978, 880-882. (c) For utilization of this interconversion for organic synthesis, see: Campbell, A. C.; Maidment, M. S.; Pick, J. H.; Stevenson, D. F. M. J. Chem. Soc., Perkin Trans, 1 1985, 1567-1576.
20. (a) For interconversion via thermolysis, see: Claisen, L.; Ewan, T. Justus Liebigs Ann. Chem. 1895, 284, 245-299. (b) For interconversion via base, see: Gedge, D. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1978, 880-882. (c) For utilization of this interconversion for organic synthesis, see: Campbell, A. C.; Maidment, M. S.; Pick, J. H.; Stevenson, D. F. M. J. Chem. Soc., Perkin Trans, 1 1985, 1567-1576.
21. This C - C bond is very susceptible to oxidative addition. Liebeskind, L. S.; Jewell, C. F., Jr. J. Organomet. Chem. 1985, 285, 305-319.
22. Similar intermediates have been proposed in unrelated processes, (a) Xu, Y.-C.; Challener, C. A.; Dragisch, V.; Brandvold, T. A.; Peterson, G. A.; Wulff, W. D.; Williard, P. G. J. Am. Chem. Soc. 1989, 111, 7269-7271. (b) Liebeskind, L. S.; Chidambaran, R. J. Am. Chem. Soc. 1987, 109, 5025-5026.
23. Similar intermediates have been proposed in unrelated processes, (a) Xu, Y.-C.; Challener, C. A.; Dragisch, V.; Brandvold, T. A.; Peterson, G. A.; Wulff, W. D.; Williard, P. G. J. Am. Chem. Soc. 1989, 111, 7269-7271. (b) Liebeskind, L. S.; Chidambaran, R. J. Am. Chem. Soc. 1987, 109, 5025-5026.
24. Anderson, J. R.; Edwards, R. L.; Whalley, A. J. S. J. Chem. Soc., Perkin Trans, 1 1982, 215-221.
25. a. Raffauf, R. F.; Zennie, T. M.; Onan, K. D.; Le Quesne, P. W. J. Org. Chem. 1984, 49, 2714-2718.
26. A similar explanation has been used to explain formation of cyclopentendiones and alkylidenefuranones in ring expansion of 4-diazoalkyl-2-cyclobuten-1-ones. Ohno, M.; Noda, M.; Yamamoto, Y.; Eguchi, S. J. Org. Chem. 1999, 64, 707-712.
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29. Gong, L.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1991, 113, 6021-6028.
30. For a general discussion of the synthesis and importance of cyclopentenediones, see refs 11, 12, 14, and 17.
31. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482-2488.
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34. Moser, E.; Fischer, E. O. J. Organomet. Chem. 1968, 13, 387-398.
35. Fischer, E. O.; Kreiter, C. G.; Kollmeier, H. J.; Müller, J.; Fischer, R. D. J. Organomet. Chem. 1971, 28, 237-258.