A novel montmorillonite-enwrapped scandium as a heterogeneous catalyst for Michael reaction

Journal of the American Chemical Society

Volumn 125, Issue 35, 2003, Pages 10486-10487

  Kawabata, Tomonori ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MONTMORILLONITE; SCANDIUM;

ACIDITY; AQUEOUS SOLUTION; ARTICLE; CATALYST; CATION TRANSPORT; CHEMICAL ANALYSIS; MICHAEL ADDITION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0041355214     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0302578     Document Type: Article

References (27)

1. Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 1-67.
2. For an excellent review on transition metal-catalyzed Michael reaction of 1,3-dicarbonyls, see: Christoffers, J. Eur. J. Org. Chem. 1998, 1259.
3. For examples of the Michael reaction in water, see: (a) Keller, E.; Feringa, B. L. Tetrahedron Lett. 1996, 37, 1879. (b) Kotsuki, H.; Arimura, K. Tetrahedron Lett. 1997, 38, 7583. (c) Mori, Y.; Kakumoto, K.; Manabe, K.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 3107. Note that the above systems generally require 1.5-3 equiv of the acceptors to achieve high yields within acceptable reaction times.
4. For examples of the Michael reaction in water, see: (a) Keller, E.; Feringa, B. L. Tetrahedron Lett. 1996, 37, 1879. (b) Kotsuki, H.; Arimura, K. Tetrahedron Lett. 1997, 38, 7583. (c) Mori, Y.; Kakumoto, K.; Manabe, K.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 3107. Note that the above systems generally require 1.5-3 equiv of the acceptors to achieve high yields within acceptable reaction times.
5. For examples of the Michael reaction in water, see: (a) Keller, E.; Feringa, B. L. Tetrahedron Lett. 1996, 37, 1879. (b) Kotsuki, H.; Arimura, K. Tetrahedron Lett. 1997, 38, 7583. (c) Mori, Y.; Kakumoto, K.; Manabe, K.; Kobayashi, S. Tetrahedron Lett. 2000, 41, 3107. Note that the above systems generally require 1.5-3 equiv of the acceptors to achieve high yields within acceptable reaction times.
6. For a review, see: Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227.
7. Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
8. For a review, see: Kobayashi, S. Eur. J. Org. Chem. 1999, 15.
9. (a) Pinnavaia, T. J. Science 1983, 220, 365.
10. (b) Laszlo, P. Science 1987, 235, 1473.
11. (a) Ebitani, K.; Kawabata, T.; Nagashima, K.; Mizugaki, T.; Kaneda, K. Green Chem. 2000, 2, 157.
12. (b) Kawabata, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2001, 42, 8329.
13. (c) Ebitani, K.; Ide, M.; Mitsudome, T.; Mizugaki, T.; Kaneda, K. Chem. Commun. 2002, 690.
14. Onaka, M. Yuki Gosei Kagaku Kyokaishi 1995, 53, 392.
15. For recent reports on heterogeneous Michael reactions using organic polymer-bound Sc catalysts, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Reetz, M. T.; Giebel, D. Angew. Chem. Int. Ed. 2000, 39, 2498. (c) Weiqiang, G.; Zhou, W.-J.; Gin, D. L. Chem. Mater. 2001, 13, 1949. Note that these systems are limited to the reaction of activated donors such as silyl enol ethers.
16. For recent reports on heterogeneous Michael reactions using organic polymer-bound Sc catalysts, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Reetz, M. T.; Giebel, D. Angew. Chem. Int. Ed. 2000, 39, 2498. (c) Weiqiang, G.; Zhou, W.-J.; Gin, D. L. Chem. Mater. 2001, 13, 1949. Note that these systems are limited to the reaction of activated donors such as silyl enol ethers.
17. For recent reports on heterogeneous Michael reactions using organic polymer-bound Sc catalysts, see: (a) Nagayama, S.; Kobayashi, S. Angew. Chem., Int. Ed. 2000, 39, 567. (b) Reetz, M. T.; Giebel, D. Angew. Chem. Int. Ed. 2000, 39, 2498. (c) Weiqiang, G.; Zhou, W.-J.; Gin, D. L. Chem. Mater. 2001, 13, 1949. Note that these systems are limited to the reaction of activated donors such as silyl enol ethers.
18. See Supporting Information for details.
19. + ions.
20. 3+-mont is comparable to that observed in hexa-coordinated scandium aqua complexes (2.11-2.12 Å); see: Cotton, S. A. Polyhedron 1999, 18, 1691.
21. Brown, P. L.; Ellis, J.; Sylva, R. N. J. Chem. Soc., Dalton Trans. 1983, 35.
22. 3+-mont expanded from 3.6 to 9.0 Å, as determined by XRD, allowing access of the substrates to the catalytic site of Sc species.
23. Fukuzumi, S.; Ohkubo, K. J. Am. Chem. Soc. 2002, 124, 10270.
24. Treatment of 1a and 1c with 2a under solvent-free conditions afforded 3a and 3c in 91% and 54% yields, respectively.
25. Manabe, K.; Iimura, S.; Sun, X.-M.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 11971.
26. -1 confirmed the formation of an acetylacetonato Sc complex; see: Singh, P. R.; Sahai, R. Inorg. Chim. Acta 1968, 2, 102.
27. 3, the activation of an acceptor by the Lewis acid sites is indispensable; see: Christoffers, J. Chem. Commun. 1997, 943.