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

✍ Scribed by Muhammad Nor Omar; Humphrey A. Moynihan; Richard J. Hamilton

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
24 KB
Volume
105
Category
Article
ISSN
1438-7697

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✦ Synopsis

Abstract

The asymmetric Sharpless epoxidation of methyl 13__S__‐hydroxy‐9__Z__, 11__E__‐octadeca‐dienoate (13__S__‐HODE, 1) with tert‐butyl hydroperoxide (TBHP) catalysed by titanium tetraisopropoxide {Ti(^i^OPr)~4~} in the presence of L(+)‐diisopropyl tartrate (L‐DIPT) gave methyl 13__S__‐hydroxy‐11__S__, 12__S__‐epoxy‐9__Z__‐octadecenoate 2 (erythro isomer) in 84% diastereomeric excess (de). The epoxidation of 1 with TBHP catalysed by Ti(^i^OPr)~4~ in the presence of D(‐)‐DIPT yielded methyl 13__S__‐hydroxy‐11R__R__12__R__‐epoxy‐9__Z__‐octadecenoate (threo isomer) 3 in 76% de.

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