Iodine promoted cyclofunctionalization reaction of 2,4-dialkenyl-1,3- dicarbonyl compounds

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 4977-4980

  Stefani, Hélio A ^a   Petragnani, Nicola ^a   Valduga, Claudéte J ^a   Brandf, Carlos A ^b  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b INSTITUTO BUTANTAN   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0030861432     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01079-4     Document Type: Article

References (20)

1. Clive, D .L. J.; Chittattu, G.; Curtis, N.; Kiel, W .A.; Wong, C. K., J. Chem. Soc., Chem. Commun. 1977, 725.
2. Bartlett, P. A., in "Asymmetric Synthesis", J.D. Morrison, Ed., Academic Press, 1984, 3, 417.
3. (a) Campos, M.M.; Petragnani, N. Chem. Ber. 1960, 93, 317.
4. (b) Brandt, C.A.; Comasseto, J.V.; Ferraz, H.M.C., Quim. Nova 1991, 14, 165.
5. Campos, M.M.; Petragnani, N., Tetrahedron Lett. 1959, 13.
6. (b) Comasseto, J.V.; Ferraz, H.M.C.; Petragnani, N.; Brandt, C.A., Tetrahedron Lett. 1987, 28, 5611.
7. (a) Antonioletti, R; Cecchini, C.; Ciani, B.; Magnanti, S., Tetrahedron Lett. 1995, 36, 9019.
8. (b) Jackson, W. P.; Ley, S. V.; Whittle, A. J., J. Chem. Soc., Chem. Commun. 1980, 1173.
9. Ferraz, H.M.C.; Oliveira, E.O.; Payret-Arrua, M.E.; Brandt, C.A. J.Org.Chem. 1995, 60, 7357.
10. (a) Vernin, G., The Chemistry of Heterocyclic Flavouring and Aroma Compounds, Horwood, E., Chichester, 1982.
11. (b) Donnelly, D.M.X.; M.J. in Comprehensive Organic Chemistry, Bird, C.W.; Cheeseman, G.W.H. Ed. Pergamon, New York, 1984, vol. 4, pp. 657.
12. Lipshutz, B.H., Chem.Rev. 1986, 86, 795.
13. Marvel, C.S.; Hager, F.D., Organic Synthesis; Wiler: New York, 1948; vol. 1, p248.
14. Johnson, A.W.; Markhan, E.; Price, R. Org. Synth. 1965, 42, 75
15. Huckin, S. N.; Weiler, L., J.Am.Chem.Soc. 1974, 96, 1082.
16. Ranu, B.C.; Bhar, S., J.Chem.Soc. Perkin Trans. I, 1992, 365.
17. For lactonization of γ,δ-unsaturated esters with electrophiles see: (a) Arnold, R.T., Lindsey, K.L., J.Am.Chem.Soc. 1953, 75, 1048,
18. (b) Do Amaral, A.T., El Seoud, O.A., Do Amaral, L., J.Org.Chem. 1975, 40, 2534.,
19. (c) Bartlett, P.A., Myerson, J., J.Am.Chem.Soc. 1978, 100, 3950.
20. 3)δ: 7.02, 9.22, 29.15, 31.53, 74.93, 82.97, 93.83, 168.82, 171.25.