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

• Main Authors: Omar, Muhammad Nor, Moynihan, Humphrey A, Hamilton, Richard J.
• Format: Article
• Language: English
• Published: Wiley 2003
• Subjects: QD Chemistry
• 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
• Institution: Universiti Islam Antarabangsa Malaysia

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.