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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| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
Wiley
2003
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| Subjects: | |
| Online Access: | http://irep.iium.edu.my/24440/1/EJLST_Omar.pdf http://irep.iium.edu.my/24440/ http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1438-9312/issues |
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| Institution: | Universiti Islam Antarabangsa Malaysia |
| Language: | English |
| Summary: | 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. |
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