Group VI metal-promoted endo-carbocyclizations via alkyne-derived metal vinylidene carbenes

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7691-7692

  McDonald, Frank E ^a   Olson, Timothy C ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENE DERIVATIVE; MOLYBDENUM;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION KINETICS; ISOMERISM; METAL BINDING; ORGANIC CHEMISTRY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0030722422     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10007-7     Document Type: Article

References (11)

1. McDonald, F. E.; Gleason, M. M. J. Am. Chem. Soc. 1996, 118, 6648, and references therein.
2. Ruthenium-catalyzed cycloisomerization of alkynyldienes to benzenoid compounds was recently reported: Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319.
3. Compounds 1 - 3 were prepared by enolization and alkylation of the simple β-dicarbonyl compound with 4-iodo-1-butyne: (a) Taylor, E. C.; Macor, J. E.; French, L. G. J. Org. Chem. 1991, 56, 1807.
4. (b) Eglington, G.; Whiting, M. C. J. Chem. Soc. 1950, 3653.
5. (c) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293.
6. 5 also produced cyclopentene 4, but in considerably lower isolated yields.
7. Other Lewis acidic metal reagents also promote exo-carbocyclizations: (a) Boaventura, M. A.; Drouin, J.; Conia, J. M. Synthesis 1983, 801.
8. (b) Forsyth, C. J.; Clardy, J. J. Am. Chem. Soc. 1990, 112, 3497.
9. (c) Monteiro, N.; Gore, J.; Balme, G. Tetrahedron 1992, 48, 10103.
10. (d) Cruciani, P.; Stammler, R.; Aubert, C.; Malacria, M. J. Org. Chem. 1996, 61, 2699.
11. (a) Compound 4 is mentioned once in the literature, produced in very low yield as a component of an inseparable mixture with the 3-cyclopentene isomer: Abram, T. S.; Baker, R.; Exon, C.; Rao, V. B. J. Chem. Soc., Perkin Trans 1 1982, 285.