Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE)
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 (er...
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| Format: | Article |
| Language: | English |
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Wiley
2003
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| Online Access: | http://irep.iium.edu.my/24440/ http://irep.iium.edu.my/24440/1/EJLST_Omar.pdf |
| _version_ | 1848779299388129280 |
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| author | Omar, Muhammad Nor Moynihan, Humphrey A Hamilton, Richard J. |
| author_facet | Omar, Muhammad Nor Moynihan, Humphrey A Hamilton, Richard J. |
| author_sort | Omar, Muhammad Nor |
| building | IIUM Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T15:15:34Z |
| format | Article |
| id | iium-24440 |
| institution | International Islamic University Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T15:15:34Z |
| publishDate | 2003 |
| publisher | Wiley |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | iium-244402013-03-01T01:47:04Z http://irep.iium.edu.my/24440/ Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE) Omar, Muhammad Nor Moynihan, Humphrey A Hamilton, Richard J. QD Chemistry 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. Wiley 2003 Article PeerReviewed application/pdf en http://irep.iium.edu.my/24440/1/EJLST_Omar.pdf 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 http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1438-9312/issues 10.1002/ejlt.200390005 |
| spellingShingle | QD Chemistry Omar, Muhammad Nor Moynihan, Humphrey A Hamilton, Richard J. Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE) |
| title | Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE) |
| title_full | Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE) |
| title_fullStr | Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE) |
| title_full_unstemmed | Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE) |
| title_short | Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE) |
| title_sort | asymmetric sharpless epoxidation of 13shydroxy-9z,11e-octadecadienoic acid (13s-hode) |
| topic | QD Chemistry |
| url | http://irep.iium.edu.my/24440/ http://irep.iium.edu.my/24440/ http://irep.iium.edu.my/24440/ http://irep.iium.edu.my/24440/1/EJLST_Omar.pdf |