Heterogeneous asymmetric epoxidation of cis-allylic alcohols: Use of polymer-supported Ti(IV)-catalyst

Tetrahedron Asymmetry

Volumn 9, Issue 12, 1998, Pages 2019-2022

  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

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; TARTARIC ACID; TERT BUTYL HYDROPEROXIDE; TITANIUM;

ARTICLE; CATALYST; ENANTIOMER; EPOXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032546887     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00188-8     Document Type: Article

References (13)

1. Rossiter, B. E. Asymmetric Synthesis, Academic Press, Orlando, FL, 1985, Vol.5, 193-246.
2. Canali, L.; Karjalainen, J. K.; Hormi, O.; Sherrington, D. C. J. Chem. Soc., Chem. Comm. 1997, 123-124.
3. Karjalainen, J. K.; Hormi, O.; Sherrington, D. C. Molecules, 1998, 3, 51-59.
4. Karjalainen, J. K.; Hormi, O.; Sherrington, D. C. Accepted for publication in Tetrahedron: Asymmetry.
5. Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ed. Ojima, I., VCH Publishers, Inc., 1993; pp. 103-158.
6. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
7. Hodge, P. Polymer-supported Asymmetric Organic Synthesis in Innovation and Perspectives in Solid Phase Synthesis; Ed. R. Epton; SPCC UK, 1990; pp. 273-292.
8. Baker, R.; Swain, C. J.; Head, J. C. J. Chem. Soc., Chem. Comm. 1986, 874.
9. (a) Mori, K.; Nakazono, Y Tetrahedron, 1986, 42(23), 6459.
10. (b) Nicolaou, K. C., Webber, S. E. J. Chem. Soc., Chem. Comm. 1985, 297.
11. Katsuki, T.; Lee, A. W. M.; Ma, V. S. J. Org. Chem. 1982, 47(7), 1373.
12. The esters used conventionally in Sharpless epoxidations are dimethyl, diethyl and diisopropyl tartrates, and, with a few subtle exeptions, all are equally effective at inducing asymmetry. See for example Johnson, R. A.; Sharpless, K. B. In Comprehensive Organic Synthesis, Vol. 7, Eds. Trost, B. M., Fleming, I., Ley, S. V. Pergamon Press, Oxford 1991, pp. 389-436
13. 6 or by HPLC using a chiral Chiralpak AS 25 cm×0.46 cm column together with a Chiralpak AS 5 cm×0.46 cm pre-column (RI-detection, eluent: n-hexane:isopropanol=9:1, flow rate: 0.5 ml/min).