Synthesis and reactivity of Michael adducts of cyclic β-ketoesters enolates with electrophilic acetylenes

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6873-6876

  Miesch, Michel ^a   Mislin, Gaëtan ^b   Franck Neumann, Michel ^b  

^a CNRS   (France)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CATALYSIS; ISOMERISM; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 0032541716     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01500-7     Document Type: Article

References (24)

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3. c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon Press 1992.
4. 2. a) Gawley, R.E. Synthesis 1976, 777-794;
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8. 3. Frew, A.J.; Proctor, G.R. J. Chem. Soc. Perkin Trans 1 1980, 1245-1250; Frew, A.J.; Proctor, G.R. Silverton, J.V. J. Chem. Soc. Perkin Trans 1 1980, 1251-1256.
9. 4. Miesch, M.; Mislin, G.; Franck-Neumann, M. Synlett 1996, 385-386.
10. 3/acetone) were already used for the Michael addition of β-ketoesters to acrylic derivatives. Barco, A.; Benetti, S.; Pollini, G.P. Synthesis 1973, 316. Ouvrard, N.; Rodriguez, J.; Santelli, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 1651-1653; Angew. Chem. 1992, 104, 1658-1659. Filippini, M.H.; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872-6882.
11. 3/acetone) were already used for the Michael addition of β-ketoesters to acrylic derivatives. Barco, A.; Benetti, S.; Pollini, G.P. Synthesis 1973, 316. Ouvrard, N.; Rodriguez, J.; Santelli, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 1651-1653; Angew. Chem. 1992, 104, 1658-1659. Filippini, M.H.; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872-6882.
12. 3/acetone) were already used for the Michael addition of β-ketoesters to acrylic derivatives. Barco, A.; Benetti, S.; Pollini, G.P. Synthesis 1973, 316. Ouvrard, N.; Rodriguez, J.; Santelli, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 1651-1653; Angew. Chem. 1992, 104, 1658-1659. Filippini, M.H.; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872-6882.
13. 3/acetone) were already used for the Michael addition of β-ketoesters to acrylic derivatives. Barco, A.; Benetti, S.; Pollini, G.P. Synthesis 1973, 316. Ouvrard, N.; Rodriguez, J.; Santelli, M. Angew. Chem. Int. Ed. Engl. 1992, 31, 1651-1653; Angew. Chem. 1992, 104, 1658-1659. Filippini, M.H.; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872-6882.
14. 6. Compounds 9E and 15E have already been prepared by another route (ketovinylation of the corresponding β-ketoesters 1 and 2): Kochetkov, N.K., Kudryashov, L.J., Gottich B.P. Tetrahedron 1961, 12, 63-65.
15. 7. a) Heathcock, C. H. In Comprehensive Organic Chemistry; Trost, B.M.; Fleming, I. Eds; Pergamon Press 1991, 2, 133-179.
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18. c) Evans, E.H.; Hewson, A.T.; March, L.A.; Nowell, I.W. J. Chem. Soc., Chem. Comm. 1982, 1342-1343; Evans, E.H.; Hewson, A.T.; March, L.A.; Nowell, I.W.; Wadsworlh, A.H. J. Chem. Soc., Perkin Trans 1 1982, 137-149;
19. d) Marshall, J.A.; Scanio, C.J.V.; Iburg, W.J. J. Org. Chem. 1967, 32, 3250-3254;
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21. 9 and 32 (n = 3). However, under the same conditions, the 1,5-diketone 33 led mainly to the bicyclo[7. 3. 1]undecane derivatives 34 and 35, the Robinson annulation product 36 being minor. (equation presented)
22. 9. Scanio, C. J. V.; Hill, L. P. Synthesis 1970, 651-652.
23. 10. Molecular models indicate clearly that the E isomers 9E - 11E cannot undergo an intramolecular aldol cyclisation, the reacting centers being too far away.
24. 3) : 13.0; 24.8; 25.2; 34.2; 34.24; 53.7; 61.5; 61.6; 114.6; 129.1; 129.7; 146.6; 171.1; 206.66