Superior amine catalysts for the Baylis-Hillman reaction: The use of DBU and its implications

Chemical Communications

Volumn , Issue 22, 1999, Pages 2311-2312

  Aggarwal, Varinder K ^a   Mereu, Andrea ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; 3 QUINUCLIDINOL; AMINE; BASE;

ARTICLE; CATALYST; CHEMICAL REACTION; REACTION TIME;

EID: 0033592809     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907754e     Document Type: Article

References (16)

1. For reviews see: D. Basavaiah, P. D. Rao and R. S. Hyma, Tetrahedron, 1996, 52, 8001; E. Ciganek, Org. React., 1997, 51, 201.
2. For reviews see: D. Basavaiah, P. D. Rao and R. S. Hyma, Tetrahedron, 1996, 52, 8001; E. Ciganek, Org. React., 1997, 51, 201.
3. V. K. Aggarwal, A. Mereu, G. J. Tarver and R. McCague, J. Org. Chem., 1998, 63, 7183; V. K. Aggarwal, G. J. Tarver and R. J. McCague, Chem. Commun., 1996, 2713.
4. V. K. Aggarwal, A. Mereu, G. J. Tarver and R. McCague, J. Org. Chem., 1998, 63, 7183; V. K. Aggarwal, G. J. Tarver and R. J. McCague, Chem. Commun., 1996, 2713.
5. J. S. Hill and N. S. Isaacs, J. Phys. Org. Chem., 1990, 3, 285.
6. DMAP has been used as a catalyst for the Baylis-Hillman reaction between cyclohex-2-en-1-one and formaldehyde but no comment was made on its effectiveness or relative rate compared to DABCO. F. Rezgui and M. M. El Gaied, Tetrahedron Lett., 1998, 39, 5965.
7. At 10 mol% loading of DBU the reaction is somewhat capricious and more reliable results are obtained using a stoichiometric amount of the base. There is a variable amount of catalyst decomposition during the course of the reaction.
8. Y. Fort, M. C. Berthe and P. Caubere, Tetrahedron, 1992, 48, 6371.
9. Cyclopent-2-en-1-one and cyclohept-2-en-1-one were both ineffective.
10. A. Foucaud and F. El Guemmout, Bull. Chim. Soc. Fr., 1989, 3, 403.
11. Reaction using DABCO reportedly failed. See: M. C. Berthe, P. Caubere and Y. Fort, Eur. Pat. Appl., 1992, EP 465,293 (Chem. Abstr., 1992, 116, 152605c); US Pat., 1994, 5,332, 836.
12. Low yields of adducts with enolisable aldehydes using DBU as a catalyst have been reported. See: D. Basavaiah and V. V. L. Gowriswari, Synth. Commun., 1987, 17, 587; P. Auvray, P. Knochel and J. F. Normant, Tetrahedron, 1988, 44, 6095.
13. Low yields of adducts with enolisable aldehydes using DBU as a catalyst have been reported. See: D. Basavaiah and V. V. L. Gowriswari, Synth. Commun., 1987, 17, 587; P. Auvray, P. Knochel and J. F. Normant, Tetrahedron, 1988, 44, 6095.
14. J. R. Hwu, G. H. Hakimalahi and C. T. Chou, Tetrahedron Lett., 1992, 33, 6469.
15. The use of DBU in the presence of 2 equiv. of 4-methoxyphenol has also been reported in a patent, although without noting its superior properties. See: K. Oohashi and S. Ido, Jpn. Kokai Koho JP, 1993, 05, 17,375 9Cl. C07B41/02 (Chem. Abstr., 1993, 118, 254552s).
16. R. J. W. Schuurman, A. Vanderlinden, R. P. F. Grimbergen, R. J. M. Nolte and H. W. Scheeren, Tetrahedron, 1996, 52, 8307.