Hydrophobic polymer-supported scandium catalyst for carbon-carbon bond-forming reactions in water

Tetrahedron

Volumn 60, Issue 35, 2004, Pages 7673-7678

  Iimura, Shinya ^a   Manabe, Kei ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

1,4 Addition; Aldol reaction; Lewis acid; Scandium; Water

Indexed keywords

KETONE DERIVATIVE; POLYSTYRENE; RESIN;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; HYDROPHOBICITY; MUKAIYAMA REACTION; PRIORITY JOURNAL; SULFONATION;

EID: 3843120103     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.083     Document Type: Article

References (37)

1. Anastas P.T., Warner J.C. Green Chemistry: Theory and Practice. 1998;Oxford University Press, New York
2. Anastas P.T., Kirchhoff M.M. Acc. Chem. Res. 35:2002;686
3. For recent examples of polymer-supported catalysts which work in water, see: (a) Nagayama S., Kobayashi S. Angew. Chem., Int. Ed. 39:2000;567
4. Uozumi Y., Danjo H., Hayashi T. Tetrahedron Lett. 38:1997;3557
5. Uozumi Y., Tanaka H., Shibatomi K. Org. Lett. 6:2004;281
6. Bergbreiter D.E., Liu Y.-S. Tetrahedron Lett. 38:1997;7843
7. Bergbreiter D.E., Case B.L., Liu Y.-S., Caraway J.W. Macromolecules. 31:1998;6053
8. Bergbreiter D.E. Chem. Rev. 102:2002;3345
9. Yamada Y.M.A., Ichinohe M., Takahashi H., Ikegami S. Org. Lett. 3:2001;1837
10. Yu L., Chen D., Li J., Wang P.G. J. Org. Chem. 62:1997;3575
11. Reetz M.T., Giebel D. Angew. Chem., Int. Ed. 39:2000;2498
12. Gu W., Zhou W.-J., Gin D.L. Chem. Mater. 13:2001;1949
13. Nishikido J., Nanbo M., Yoshida A., Nakajima H., Matsumoto Y., Mikami K. Synlett. 2002;1613
14. Kawabata T., Mizugaki T., Ebitani K., Kaneda K. J. Am. Chem. Soc. 125:2003;10486
15. Usui Y., Sato K., Tanaka M. Angew. Chem., Int. Ed. 42:2003;5623
16. For water-tolerant solid acid catalysts: Okuhara T. Chem. Rev. 102:2002;3641. and references therein
17. Manabe K., Kobayashi S. Adv. Synth. Catal. 344:2002;270
18. Iimura S., Manabe K., Kobayashi S. Org. Lett. 5:2003;101
19. Iimura S., Nobutou D., Manabe K., Kobayashi S. Chem. Commun. 2003;1644
20. Iimura S., Manabe K., Kobayashi S. Org. Biomol. Chem. 1:2003;2416
21. Iimura S., Manabe K., Kobayashi S. J. Org. Chem. 68:2003;8723
22. Mukaiyama T., Banno K., Narasaka K. J. Am. Chem. Soc. 96:1974;7503
23. Mukaiyama T. Org. React. 28:1982;203
24. Mahrwald R. Chem. Rev. 99:1999;1095
25. Kobayashi S. Eur. J. Org. Chem. 1999;15
26. Kobayashi S., Sugiura M., Kitagawa H., Lam W.W.-L. Chem. Rev. 102:2002;2227
27. Manabe K., Mori Y., Wakabayashi T., Nagayama S., Kobayashi S. J. Am. Chem. Soc. 122:2000;7202
28. The commercially available PS-Sc and PS-Yb were purchased from Aldrich and Novabiochem, respectively
29. Kobayashi S., Hachiya I., Ishitani H., Araki M. Synlett. 1993;472
30. 2
31. Narasaka K., Soai K., Aikawa Y., Mukaiyama T. Bull. Chem. Soc. Jpn. 49:1976;779
32. For the unique molecular discrimination in the reaction of α,β-unsaturated ketones with ketene silyl acetals in an organic solvent, see: Hanyuda K., Hirai K., Nakai T. Synlett. 1997;31
33. Manabe K., Aoyama N., Kobayashi S. Adv. Synth. Catal. 343:2001;174
34. Kobayashi S., Hachiya I. J. Org. Chem. 59:1994;3590
35. Kobayashi S., Hachiya I., Yamanoi Y. Bull. Chem. Soc. Jpn. 67:1994;2342
36. Loh T.P., Feng L.C., Wei L.L. Tetrahedron. 56:2000;7309
37. Denmark S.E., Wong K.-T., Stavenger R.A. J. Am. Chem. Soc. 119:1997;2333