Lewis acid catalysis in micellar systems. Sc(OTf)3-catalyzed aqueous aldol reactions of silyl enol ethers with aldehydes in the presence of a surfactant

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4559-4562

  Kobayashi, Shu ^a   Wakabayashi, Takeshi ^a   Nagayama, Satoshi ^a   Oyamada, Hidekazu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ETHER DERIVATIVE; SCANDIUM; SURFACTANT;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; MICELLE;

EID: 0030913328     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00854-X     Document Type: Article

References (21)

1. Review: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023.
2. (b) Lubineau, A.; Ange, J.; Queneau, Y. Synthesis 1994, 741.
3. (a) Mukaiyama, T.; Narasaka, K.; Banno, T. Chem Lett. 1973, 1011.
4. (b) Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503.
5. (c) Mukaiyama, T. Org. React. 1982, 28, 203.
6. (a) Kobayashi, S. Chem. Lett. 1991, 2187.
7. (b) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 1625.
8. (c) Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590.
9. (d) Kobayashi, S. Synlett 1994, 689.
10. Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull Chem. Soc. Jpn. 1994, 67, 2342.
11. Lubineau reported water-promoted aldol reactions of silyl enol ethers with aldehydes, however, the yields and the substrate scope were not satisfactory, (a) Lubineau, A. J. Org. Chem. 1986, 51, 2142.
12. (b) Lubineau, A.; Meyer, E. Tetrahedron 1988, 44, 6065.
13. 3-catalyzed Mukaiyama aldol reactions in water were reported. However, these reactions could not be reproduced in our hands. Loh, T.-P.; Pei, J.; Cao, G.-Q. J. Chem. Soc., Chem. Commun. 1996, 1819.
14. In the absence of the Lewis acid and the surfactant (water-promoted conditions), only 20% yield of the aldol adduct was isolated after 48 h, while a 33% yield of the aldol adduct was obtained after 48 h in the absence of the Lewis acid in an aqueous solution of SDS.
15. Although several organic reactions in micelles were reported, there was no report on Lewis acid catalysis in micelles, to the best of our knowledge. In addition, judging from the amount of the surfactant used in the present case, the aldol reaction would not proceed not only in micelle. Precise reaction mechanism is now under investigations. (a) Fendler, J. H.; Fendler, E. J. Catalysis in Micellar and Macromolecular Systems, Academic Press: London, 1975.
16. (b) Holland, P. M.; Rubingh, D. N., Eds. Mixed Surfactant Systems, ACS: Washington, DC, 1992.
17. (c) Cramer, C. J.; Truhlar, D. G., Eds. Structure and Reactivity in Aqueous Solution, ACS: Washington, DC, 1994.
18. (d) Sabatini, D. A.; Knox, R. C.; Harwell, J. H., Eds. Surfactant-Enhanced Subsurface Remediation, ACS: Washington, DC, 1994.
19. Hydrolysis of silyl enol ether 1 took place when lower yields were observed in Table 1.
20. Cf. Kobayashi, S. Hachiya, I.; Takahori, T. Synthesis 1993, 371.
21. The anion exchange resin treatment was not needed when TritonX-100 was used as a surfactant.