Selective aldol reactions of acetals on mesoporous silica catalyst

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 299-301

  Ishitani, Haruro ^a   Iwamoto, Masakazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Acetal; Aldol reaction; MCM 41; Solid acid

Indexed keywords

ACETAL DERIVATIVE; ALDEHYDE; CARBONYL DERIVATIVE; SILICON DIOXIDE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; POROSITY;

EID: 0037420991     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02563-7     Document Type: Article

References (30)

1. Fine Chemicals Through Heterogeneous Catalysis; Sheldon, R. A.; van Bekkum, H., Eds.; Wiley-VCH: Weinheim, New York, 2001.
2. Tanaka Y., Sawamura N., Iwamoto M. Tetrahedron Lett. 39:1998;9457.
3. Yamamoto T., Tanaka T., Funabiki T., Yoshida S. J. Phys. Chem. B. 102:1998;5830.
4. Itoh A., Kodama T., Maeda S., Masaki Y. Tetrahedron Lett. 39:1998;9461.
5. Kloetstra K.R., van Bekkum H. J. Chem. Res. Synop. 1:1995;26.
6. Shinoda T., Izumi Y., Onaka M. J. Chem. Soc., Chem. Commun. 1995;1801.
7. Corma A. Chem. Rev. 97:1997;2373.
8. Sayari A. Chem. Meter. 8:1995;1840.
9. van Bekkum H., Kloetstra K.R. Stud. Surf. Sci. Catal. 117:1998;171.
10. Mukaiyama T., Narasaka K., Banno K. Chem. Lett. 1973;1012.
11. Mukaiyama T. Org. React. 28:1982;203.
12. Mahrwald R. Chem. Rev. 99:1999;1095.
13. Mukaiyama T., Murakami M. Synthesis. 1987;1043.
14. Murata S., Suzuki M., Noyori R. Tetrahedron. 44:1988;4259.
15. Sato T., Otera J., Nozaki H. J. Am. Chem. Soc. 112:1990;901.
16. Chen J.-X., Sakamoto K., Orita A., Otera J. Tetrahedron. 54:1998;8411.
17. Kawai M., Onaka M., Izumi Y. Bull. Chem. Soc. Jpn. 61:1988;1237.
18. Loh T.-P., Li X.-R. Tetrahedron. 55:1999;10789.
19. Aldol reactions on metal ion-modified MCM-41 or FSM-16 were already reported: (a) Kloetstra, K. R.; van Bekkum, H. J. Chem. Soc., Chem. Commun. 1995, 1005; (b) Matsuhashi, H.; Tanaka, M.; Nakamura, H.; Arata, K. Appl. Catal. A 2001, 208, 1.
20. Aldol reactions on metal ion-modified MCM-41 or FSM-16 were already reported: (a) Kloetstra, K. R.; van Bekkum, H. J. Chem. Soc., Chem. Commun. 1995, 1005; (b) Matsuhashi, H.; Tanaka, M.; Nakamura, H.; Arata, K. Appl. Catal. A 2001, 208, 1.
21. Abe T., Tachibana Y., Uematsu T., Iwamoto M. J. Chem. Soc., Chem. Commun. 1995;1617.
22. Benzaldehyde dimethylacetal was conveniently prepared by our method, see: Ref. 2a.
23. The syn/anti-selectivity was mostly 50/50-60/40.
24. Sakurai H., Sasaki K., Hosomi A. Bull. Chem. Soc. Jpn. 56:1983;3195.
25. Mukaiyama T., Iwakiri H. Chem. Lett. 1985;1363.
26. Murakami M., Minamikawa H., Mukaiyama T. Chem. Lett. 1987;1051.
27. Trehan A., Vij A., Walia M., Kaur G., Verma R.D., Trehan S. Tetrahedron Lett. 34:1993;7335.
28. Le Roux C., Laurent-Robert C.H., Dubac L.J. Synlett. 1998;1249.
29. 2/g.
30. 2/g.