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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Wiley
2003
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| Online Access: | 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 |
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eprints |
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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 |
| repository_type |
Digital Repository |
| institution_category |
Local University |
| institution |
International Islamic University Malaysia |
| building |
IIUM Repository |
| collection |
Online Access |
| language |
English |
| topic |
QD Chemistry |
| spellingShingle |
QD Chemistry Omar, Muhammad Nor Moynihan, Humphrey A Hamilton, Richard J. Asymmetric Sharpless epoxidation of 13Shydroxy-9Z,11E-octadecadienoic acid (13S-HODE) |
| 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. |
| format |
Article |
| 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 |
| title |
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_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_sort |
asymmetric sharpless epoxidation of 13shydroxy-9z,11e-octadecadienoic acid (13s-hode) |
| publisher |
Wiley |
| publishDate |
2003 |
| 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 |
| first_indexed |
2023-09-18T20:36:38Z |
| last_indexed |
2023-09-18T20:36:38Z |
| _version_ |
1777409089843757056 |