Coupling of Fischer Carbene Complexes with Conjugated Enyne-Aldehydes and Ketones: A Novel Synthesis of Furan Derivatives

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4564-4565

  Herndon, James W ^a   Wang, Haixia ^b  

^a NEW MEXICO STATE UNIVERSITY   (United States)

^b Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001068306     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9803939     Document Type: Article

References (22)

1. Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, pp 469-547.
2. (a) Wulff, W. D.; Kaesler, R. W.; Peterson, G. A.; Tang, P.-C. J. Am. Chem. Soc. 1985, 107, 1060-1062.
3. (b) Herndon, J. W.; Hayford, A. Organometallics 1995, 14, 1556-1558.
4. (c) Wulff, W. D. Adv. Met.-Org. Chem. 1989, 1, 209-393.
5. (d) Merlic, C. A.; Xu, D. J. Am. Chem. Soc. 1991, 113, 7418-7420.
6. Alternatively, this intermediate could be accessed through coupling of alkynes with acylcarbene complexes. This class of compounds is rare, (a) Aumann, R.; Heinen, H. Chem. Ber. 1986, 117, 3801-3811. (b) Aumann, R.; Fischer, E. O. Chem. Ber. 1968, 101, 954-962.
7. Alternatively, this intermediate could be accessed through coupling of alkynes with acylcarbene complexes. This class of compounds is rare, (a) Aumann, R.; Heinen, H. Chem. Ber. 1986, 117, 3801-3811. (b) Aumann, R.; Fischer, E. O. Chem. Ber. 1968, 101, 954-962.
8. Wang, K. K.; Liu, B.; Lu, Y. Tetrahedron Lett. 1995, 36, 3785-3788.
9. A similar process has been proposed for rhodium carbenoids derived from diazo compounds. Padwa, A.; Kinder, F. R. J. Org. Chem. 1993, 50, 21-28.
10. A variety of compound classes have been reported from the coupling of carbene complex 9 with simple alkynes. (a) For a detailed discussion, see: Challener, C. A.; Wulff, W. D.; Anderson, B. A.; Chamberlin, S. A.; Faron, K. L.; Kim, O. K.; Murray, C. K.; Xu, Y.-C.; Yang, D. C.; Darling, S. D. J. Am. Chem. Soc. 1993, 115, 1359-1376 and references therein, (b) Polymerization reactions are also possible. Katz, T. J.; Lee, S. J. J. Am. Chem. Soc. 1980, 102, 422-424.
11. A variety of compound classes have been reported from the coupling of carbene complex 9 with simple alkynes. (a) For a detailed discussion, see: Challener, C. A.; Wulff, W. D.; Anderson, B. A.; Chamberlin, S. A.; Faron, K. L.; Kim, O. K.; Murray, C. K.; Xu, Y.-C.; Yang, D. C.; Darling, S. D. J. Am. Chem. Soc. 1993, 115, 1359-1376 and references therein, (b) Polymerization reactions are also possible. Katz, T. J.; Lee, S. J. J. Am. Chem. Soc. 1980, 102, 422-424.
12. (a) In another case where an ester carbonyl group and alkyne are in a similar relative position (no conjugating alkene), formation of a carbonyl ylide derivative was not noted. Wulff, W. D.; McCallum, J. S.; Kunng, F.A. J. Am. Chem. Soc. 1988, 110, 7419-7434.
13. (b) Esters are less likely to cyclize to carbonyl ylide intermediates than ketones. Dean, D. C.; Krumpe, K. E.; Padwa, A. J. Chem. Soc., Chem. Commun. 1989, 921-922.
14. Houpis, I. N. Tetrahedron Lett. 1991, 32, 6675-6678.
15. For a review of syntheses of furan derivatives, see: Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Bird, C. W., Cheeseman, G. W. H., Eds.; Pergammon: Oxford, 1984; Vol. 4, pp 657-712.
16. (a) For a general discussion of furan formation from carbene complexes and alkynes, see: McCallum, J. S.; Kunng, F.-A.; Gilbertson, S. R.; Wulff, W. D. Organometallics 1988, 7, 2346-2360.
17. (b) Wulff, W. D.; Gilbertson, S. R.; Springer, J. P. J. Am. Chem. Soc. 1986, 108, 520-522.
18. (c) Semmelhack M. F.; Park, J. Organometallics 1986, 5, 2550-2552.
19. (d) Dötz, K. H.; Dietz, R. H.; Neuberger, D. Chem. Ber. 1979, 112, 1486-1490.
20. (e) Parlier, A.; Rudler, M.; Rudler, H.; Goumont, R.; Daran, J. C.; Vaissermann, J. Organometallics 1995, 14, 2760-2774.
21. (f) For a process involving Fischer carbene complex intermediates, see: McDonald, F. E.; Schultz, C. C. J. Am. Chem. Soc. 1994, 116, 9363-9364.
22. (g) For another process involving enyne oxides, see: Marshall, J. A.; DuBay, W. J. J. Am. Chem. Soc. 1992, 114, 1450-1456.