Synthesis of alkylidenecyclopentenones and dialkylidenecyclopentenones via the coupling of propargylic alcohol and 2-alkyne-1,4-diol derivatives with cyclopropylcarbene-chromium complexes

Tetrahedron

Volumn 56, Issue 28, 2000, Pages 4985-4993

  Herndon, James W ^a   Zhu, Jin ^a   Sampedro, Diego ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

Alkylidenecyclopentenones; Coupling reaction; Cyclopropylcarbene chromium complexes; Dialkylidenecyclopentenones

Indexed keywords

ALCOHOL DERIVATIVE; ALKYLIDENECYCLOPENTENONE DERIVATIVE; CARBENE; CHROMIUM DERIVATIVE; CYCLOPENTENONE DERIVATIVE; CYCLOPROPANE DERIVATIVE; DIALKYLIDENECYCLOPENTENONE DERIVATIVE; UNCLASSIFIED DRUG;

COMPLEX FORMATION; CONFERENCE PAPER; MOLECULAR INTERACTION; PRIORITY JOURNAL; SYNTHESIS; UNITED STATES;

EID: 85047700412     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00212-X     Document Type: Article

References (28)

1. For the latest reference, see: Yan, J.; Zhu, J.; Matasi, J. J.; Herndon, J. W. J. Org. Chem. 1999, 64, 1291-1301.
2. For a detailed mechanistic discussion, see: Tumer, S. U.; Herndon, J. W.; McMullen, L. A. J. Am. Chem. Soc. 1992, 114, 8394-8404.
3. For a mechanistically unrelated route to similar cyclopentenones using alkynes and simple carbene complexes, see: (a) 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. (b) Harvey, D. F.; Grenzer, E. M.; Gantzel, P. K. J. Am. Chem. Soc. 1994, 116, 6719-6732.
4. For a mechanistically unrelated route to similar cyclopentenones using alkynes and simple carbene complexes, see: (a) 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. (b) Harvey, D. F.; Grenzer, E. M.; Gantzel, P. K. J. Am. Chem. Soc. 1994, 116, 6719-6732.
5. Herndon J.W., Patel P.P. Tetrahedron Lett. 38:1997;59-62.
6. Herndon J.W., Tumer S.U. Tetrahedron Lett. 34:1989;95-96.
7. Herndon J.W., Matasi J.J. J. Org. Chem. 55:1990;786-788.
8. For a preliminary account of this work, see: Herndon, J. W.; Zhu, J. Org. Lett. 1999, 1, 15-18.
9. This process is analogous to the final step in the synthesis of fulvenes from cyclopentadienides and carbonyl compounds. Bergman, E. D.; Chem. Rev. 1968, 68, 41-84.
10. For a more detailed discussion of the synthetic utility of alkylidenecyclopentenones, see: Lola, D.; Belakovs, S.; Gavars, M.; Turovskis, I.; Kemme, A. Tetrahedron 1998, 54, 1589-1600.
11. (a) For Pauson-Khand-type approaches, see: Brummond, K. M.; Wan, H.; Kent, J. L. J. Org. Chem. 1998, 63, 6535-6545 and references therein.
12. (b) Eaton, B. E.; Rollman, B.; Kaduk, J. A. J. Am. Chem. Soc. 1992, 114, 6245-6246.
13. (c) Ihle, N. C.; Heathcock, C. H. J. Org. Chem. 1993, 58, 560-563.
14. (d) Flynn, B. L.; de Meijere, A. J. Org. Chem. 1999, 64, 400-404.
15. (e) Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130-4135.
16. Kascheres A., Kascheres C., Braga A.C.H. J. Org. Chem. 7:1993;1702-1703.
17. Simple 5-alkylidene-2-cyclopentenones do not appear to undergo this isomerization, but are sometimes reduced under the reaction conditions. Matasi, J. J.; Yan, J.; Herndon, J. W. Inorg. Chim. Acta 1999, 296, 273-277.
18. Negishi E., Coperet C., Ma S., Mita T., Sugihara T., Tour J.M. J. Am. Chem. Soc. 118:1996;5904-5918.
19. Herndon J.W., Zora M., Patel P.P., Chatterjee G., Matasi J.J., Tumer S.U. Tetrahedron. 53:1993;5507-5530.
20. Chan K.S., Peterson G.A., Brandvold T.A., Faron K.L., Challener C.A., Hyldahl C., Wulff W.D. J. Organomet. Chem. 334:1987;9-56.
21. (a) Strongly coordinating phosphine ligands might compete with the alkyne in the initial complexation step of the reaction. For a detailed mechanistic discussion of the coupling of alkynes and carbene complexes, see: Wulff, W. D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1065-1113.
22. (b) The lower reactivity toward alkynes of some phosphine-substituted derivatives of Fischer carbene complexes is known. Xu. Y. C.; Wulff, W. D. J. Org. Chem. 1987, 52, 3263-3275.
23. Isomerization of alkenes and dienes via iron-carbonyls is well-documented. King, R. B. In The Organic Chemistry of Iron; Koerner von Gustorf, E. A., Grevels, F. W., Fischler, I., Eds.; Academic: New York, 1978; Vol. I, pp 525-627.
24. This compound was prepared according to the following sequence: (1) Sonogashira coupling of β-bromostyrene and propargyl alcohol, (2) Swern oxidation, and (3) the resulting aldehyde was transformed to the diol derivative according to the sequence used for the coupling of 19-20B.
25. This compound was prepared via Sonogashira coupling of propargyl alcohol and iodobenzene.
26. This compound was prepared according to the following sequence: (1) Sonogashira coupling of β-bromostyrene and propargyl alcohol followed by (2) acetylation using acetyl chloride and pyridine.
27. This compound was prepared by acetylation (acetyl chloride/pyridine) of commercially available 3-hexyne-2,4-diol, which is a mixture of meso and D, L isomers.
28. This compound was prepared via the following sequence: (1) deprotonation of phenyl propargyl ether (commercially available from GFS chemicals) with n-butyllithium followed by addition of acetaldehyde, and (2) acetylation with acetyl chloride/pyridine.