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Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE)

Omar, Muhammad Nor and Moynihan, Humphrey A and Hamilton, Richard J. (2003) Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE). European Journal of Lipid Science and Technology, 105 (1). pp. 43-44. ISSN 1438-9312

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Abstract

The asymmetric Sharpless epoxidation of methyl 13S-hydroxy-9Z,11E-octadecadienoate (13S-HODE, 1) with tert-butyl hydroperoxide (TBHP) catalysed by titanium tetraisopropoxide {Ti(iOPr)4} in the presence of L(+)-diisopropyl tartrate (L-DIPT) gave methyl 13S-hydroxy-11S,12S-epoxy-9Z-octadecenoate 2 (erythro isomer) in 84% diastereomeric excess (de). The epoxidation of 1 with TBHP catalysed by Ti(iOPr)4 in the presence of D(-)-DIPT yielded methyl 13S-hydroxy-11R,12R-epoxy-9Z-octadecenoate (threo isomer) 3 in 76% de.

Item Type: Article (Journal)
Additional Information: 5626/24440
Uncontrolled Keywords: 13S-HODE; Sharpless epoxidation
Subjects: Q Science > QD Chemistry
Kulliyyahs/Centres/Divisions/Institutes: Kulliyyah of Science > Department of Biotechnology
Depositing User: Prof Dr Muhammad Nor Omar
Date Deposited: 01 Mar 2013 09:47
Last Modified: 01 Mar 2013 09:47
URI: http://irep.iium.edu.my/id/eprint/24440

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