Yb(OTf)3-catalyzed Michael addition reactions of β-ketoesters on silica gel supports and at high pressure

Tetrahedron Letters

Volumn 38, Issue 43, 1997, Pages 7583-7586

  Kotsuki, Hiyoshizo ^a   Arimura, Koji ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; INDAN DERIVATIVE; KETONE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS;

EID: 0030761766     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01788-7     Document Type: Article

References (27)

1. High Pressure Organic Chemistry. Part 21. For Part 20, see: Kotsuki, H.; Teraguchi, M.; Shimomoto, N.; Ochi, M. Tetrahedron Lett. 1996, 37, 3727-3730.
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3. Bergman, E.D.; Ginsburg, D.; Pappo, R. Org. React. 1959, 10, 595-623. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis, Pergamon Press: Oxford, 1992.
4. Kobayashi, S. Synlett 1994, 689-701; Kobayashi, S. Yuki Gosei Kagaku Kyokai-shi 1995, 53, 370-380.
5. Kobayashi, S. Synlett 1994, 689-701; Kobayashi, S. Yuki Gosei Kagaku Kyokai-shi 1995, 53, 370-380.
6. Keller, E.; Feringa, B.L. Tetrahedron Lett. 1996, 37, 1879-1882. We thank Dr. Keller for informing us the details of their reactions. See also: Keller, E.; Feringa, B.L. Synlett 1997, 842-844; Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572.
7. Keller, E.; Feringa, B.L. Tetrahedron Lett. 1996, 37, 1879-1882. We thank Dr. Keller for informing us the details of their reactions. See also: Keller, E.; Feringa, B.L. Synlett 1997, 842-844; Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572.
8. Keller, E.; Feringa, B.L. Tetrahedron Lett. 1996, 37, 1879-1882. We thank Dr. Keller for informing us the details of their reactions. See also: Keller, E.; Feringa, B.L. Synlett 1997, 842-844; Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572.
9. Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. 1996, 61, 984-990; Kotsuki, H.; Shimanouchi, T. Tetrahedron Lett. 1996, 37, 1845-1848.
10. Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. 1996, 61, 984-990; Kotsuki, H.; Shimanouchi, T. Tetrahedron Lett. 1996, 37, 1845-1848.
11. For some other applications of lanthanide catalysts to high pressure transformations, see: Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601; Posner, G.H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J.C.; Ruano, J.L.G.; Cabrejas, L.M.M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D.A.L.; Scheeren, H.W. ibid. 1995, 51, 8383-8388; Jenner, G. Tetrahedron Lett. 1996, 37, 3691-3694.
12. For some other applications of lanthanide catalysts to high pressure transformations, see: Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601; Posner, G.H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J.C.; Ruano, J.L.G.; Cabrejas, L.M.M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D.A.L.; Scheeren, H.W. ibid. 1995, 51, 8383-8388; Jenner, G. Tetrahedron Lett. 1996, 37, 3691-3694.
13. For some other applications of lanthanide catalysts to high pressure transformations, see: Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601; Posner, G.H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J.C.; Ruano, J.L.G.; Cabrejas, L.M.M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D.A.L.; Scheeren, H.W. ibid. 1995, 51, 8383-8388; Jenner, G. Tetrahedron Lett. 1996, 37, 3691-3694.
14. For some other applications of lanthanide catalysts to high pressure transformations, see: Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601; Posner, G.H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J.C.; Ruano, J.L.G.; Cabrejas, L.M.M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D.A.L.; Scheeren, H.W. ibid. 1995, 51, 8383-8388; Jenner, G. Tetrahedron Lett. 1996, 37, 3691-3694.
15. For some other applications of lanthanide catalysts to high pressure transformations, see: Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601; Posner, G.H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J.C.; Ruano, J.L.G.; Cabrejas, L.M.M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D.A.L.; Scheeren, H.W. ibid. 1995, 51, 8383-8388; Jenner, G. Tetrahedron Lett. 1996, 37, 3691-3694.
16. For some other applications of lanthanide catalysts to high pressure transformations, see: Meguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597-2601; Posner, G.H.; Ishihara, Y. Tetrahedron Lett. 1994, 35, 7545-7548; Jenner, G. ibid. 1995, 36, 233-236; Carretero, J.C.; Ruano, J.L.G.; Cabrejas, L.M.M. Tetrahedron 1995, 51, 8323-8332; Vandenput, D.A.L.; Scheeren, H.W. ibid. 1995, 51, 8383-8388; Jenner, G. Tetrahedron Lett. 1996, 37, 3691-3694.
17. For some recent examples of solvent-free Michael addition reactions of β-ketoesters, see: Christoffers, J. J. Chem. Soc., Chem. Commun. 1997, 943-944; Soriente, A.; Spinella, A.; De Rosa, M.; Giordano, M.; Scettri, A. Tetrahedron Lett. 1997, 38, 289-290; Baruah, B.; Boruah, A.; Prajapati, D.; Sandhu, J.S. ibid. 1997, 38, 1449-1450.
18. For some recent examples of solvent-free Michael addition reactions of β-ketoesters, see: Christoffers, J. J. Chem. Soc., Chem. Commun. 1997, 943-944; Soriente, A.; Spinella, A.; De Rosa, M.; Giordano, M.; Scettri, A. Tetrahedron Lett. 1997, 38, 289-290; Baruah, B.; Boruah, A.; Prajapati, D.; Sandhu, J.S. ibid. 1997, 38, 1449-1450.
19. For some recent examples of solvent-free Michael addition reactions of β-ketoesters, see: Christoffers, J. J. Chem. Soc., Chem. Commun. 1997, 943-944; Soriente, A.; Spinella, A.; De Rosa, M.; Giordano, M.; Scettri, A. Tetrahedron Lett. 1997, 38, 289-290; Baruah, B.; Boruah, A.; Prajapati, D.; Sandhu, J.S. ibid. 1997, 38, 1449-1450.
20. Review: Basiuk, V.A. Russ. Chem. Rev. 1995, 64, 1003-1019.
21. During this study a related work on the use of rare earth salts on silica gel has been reported: Bianco, A.; Brufani, M.; Melchioni, C.; Romagnoli, P. Tetrahedron Lett. 1997, 38, 651-652. See also: Laszlo, P.; Montaufier, M.-T.; Randriamahefa, S.L. ibid. 1990, 31, 4867-4870.
22. During this study a related work on the use of rare earth salts on silica gel has been reported: Bianco, A.; Brufani, M.; Melchioni, C.; Romagnoli, P. Tetrahedron Lett. 1997, 38, 651-652. See also: Laszlo, P.; Montaufier, M.-T.; Randriamahefa, S.L. ibid. 1990, 31, 4867-4870.
23. No remarkable difference in reactivity was observed after drying at 200 °C for 5 h.
24. 3 catalyst was rather drastic to control the reaction, giving 3 in 78% yield after 2 days at rt. We could not recognize the catalytic activity of silica gel itself for the present purpose: a trace amount of 3 was only detected after 1 week at rt.
25. Satisfactory spectral data were obtained for all new compounds.
26. At high pressure the use of acrylonitrile as an acceptor resulted in polymerization.
27. 2. Evaporation of the solvent gave a crude product, which was purified as above to afford the desired Michael adduct.