Efficient polymer-supported sharpless alkene epoxidation catalyst

Molecules

Volumn 3, Issue 3, 1998, Pages 51-59

  Karjalainen, Jaana K ^a   Hormi, Osmo E O ^a   Sherrington, David C ^b  

^a UNIVERSITY OF OULU   (Finland)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Asymmetric epoxidation; Polymer supported catalyst; Sharpless epoxidation

Indexed keywords

ALKENE; ESTER DERIVATIVE; HYDROPEROXIDE; LIGAND; POLYMER;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMISTRY; ENANTIOMER; EPOXIDATION; FILTRATION; REACTION ANALYSIS;

EID: 0003049367     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/30300051     Document Type: Article

References (31)

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7. See ref. 2. (a) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 3003-3006. (b) Jacobsen, E. N.; Zhang, W.; Muci, J. R.; Echer, J. R.; Deng L. J. Am. Chem. Soc. 1991, 113, 7063-7064. (c) Lohray, B. B.; Thomas, A.; Chittari, P.; Ahuja, J. R.; Dhal, P. K. Tetrahedron Lett. 1992, 33, 5453-5456. (d) Pini, D.; Petri, A.; Salvadori, P. Tetrahedron Asymm. 1993, 4, 2351-2354. (e) Itsuno, S.; Koizumi, T.; Okumura, C.; Ito, K. Synthesis 1995, 150-152. (f) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633.
8. See ref. 2. (a) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 3003-3006. (b) Jacobsen, E. N.; Zhang, W.; Muci, J. R.; Echer, J. R.; Deng L. J. Am. Chem. Soc. 1991, 113, 7063-7064. (c) Lohray, B. B.; Thomas, A.; Chittari, P.; Ahuja, J. R.; Dhal, P. K. Tetrahedron Lett. 1992, 33, 5453-5456. (d) Pini, D.; Petri, A.; Salvadori, P. Tetrahedron Asymm. 1993, 4, 2351-2354. (e) Itsuno, S.; Koizumi, T.; Okumura, C.; Ito, K. Synthesis 1995, 150-152. (f) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633.
9. See ref. 2. (a) Kim, B. M.; Sharpless, K. B. Tetrahedron Lett. 1990, 31, 3003-3006. (b) Jacobsen, E. N.; Zhang, W.; Muci, J. R.; Echer, J. R.; Deng L. J. Am. Chem. Soc. 1991, 113, 7063-7064. (c) Lohray, B. B.; Thomas, A.; Chittari, P.; Ahuja, J. R.; Dhal, P. K. Tetrahedron Lett. 1992, 33, 5453-5456. (d) Pini, D.; Petri, A.; Salvadori, P. Tetrahedron Asymm. 1993, 4, 2351-2354. (e) Itsuno, S.; Koizumi, T.; Okumura, C.; Ito, K. Synthesis 1995, 150-152. (f) Han, H.; Janda, K. D. J. Am. Chem. Soc. 1996, 118, 7632-7633.
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17. 1H NMR spectra. Some polymer batches contained toluene-p-sulfonic acid.
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20. 20+8.5° (neat).
21. 25+9 (c 1.6, THF).
22. No attempt was made to re-precipitate and re-use these polymers.
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26. The reaction mixtures were kept at - 20°C overnight since it was observed that reactions continued slowly also without strirring. However, this procedure did not have any effect on lower/higher enantioselectivity.
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30. The research on development of the reusable heterogeneous epoxidation catalyst is under the investication in our laboratory.
31. Hill, J. G.; Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3607-3608.