Abstract
A method has been developed for the acylation of dicobalt hexacarbonyl (DCHC) complexes of conjugated enynes with α, β-unsaturated acylium salts as a general route to DCHC complexes of 3-keto-1,6-enynes. Conditions have been found for the selective Grignard reaction or hydride reduction of the carbonyl group of the latter. The method has been found to be applicable to [2+2+1]-cycloaddition at a sorbent surface for the DCHC complexes of a variety of functionally substituted 1,6-enyne substrates. A novel convergent strategy is proposed for the synthesis of substituted bicyclo[3.3.0]octanes by steps involving cationic acylation of the DCHC complexes of conjugated enynes with α,β-unsaturated acylium salts, modification of the carbonyl function in the resulting adducts and intramolecular [2+2+1]-cycloaddition.
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Literature cited
L. A. Paguette, Top. Curr. Chem., 119 (1984).
P. L. Pauson and I. U. Khand, Ann. New York Acad. Sci.,295, 2 (1977).
M. C. Croudace and N. E. Shore, J. Org. Chenu,46, 5436 (1981).
P. Magnus and C. Exon, Tetrahedron,41, 5861 (1985).
D. H. Hua and M. J. Coulter, Tetrahedron Lett.,28, 5465 (1987).
V. A. Smit, A. S. Gybin, S. P. Simonyan, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 11, 2650 (1985).
V. A. Smit, S. O. Simonyan, V. A. Tarasov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2796 (1988).
W. A. Smit, A. S. Gybin, A. S. Shashkov, et al., Tetrahedron Lett.,27, 1241 (1986).
A. A. Schegolev, W. A. Smit, Y. B. Kalyan, et al., Tetrahedron Lett.,23, 4419 (1982).
G. S. Mikaelyan, A. S. Gybin, and V. A. Smit, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2277 (1985).
W. A. Smit, A. A. Schegolev, A. S. Gybin, et al., Synthesis, 887 (1984).
P. L. Pauson, Tetrahedron,41, 5585 (1985).
T. Tsunoda, M. Suzuki, R. Noyor, et al., Tetrahedron Lett.,21, 1357 (1980).
R. Sterzycky, Synthesis, 724 (1979).
A. Gemal and J.-L. Luche, J. Am. Chem. Soc.,103, 5454 (1981).
C. Almansa and E. Carceller, Synth. Commun.,18, 381 (1988).
P. Magnus and L. M. Principle, Tetrahedron Lett.,26, 4851 (1985).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2756–2764, December, 1989.
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Gybin, A.S., Smit, V.A., Veretenov, A.L. et al. Dicobalt hexacarbonyl complexes of conjugated enynes as equivalents of tetradentate synthons for the preparation of bicyclo [3.3.0] octanes. Russ Chem Bull 38, 2521–2529 (1989). https://doi.org/10.1007/BF00962438
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DOI: https://doi.org/10.1007/BF00962438