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

Muhammad Nor Omar; Humphrey A. Moynihan; Richard J. Hamilton

doi:10.1002/ejlt.200390005

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

Muhammad Nor Omar
, Humphrey A. Moynihan
, Richard J. Hamilton

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	43-44
Number of pages	2
Journal	European Journal of Lipid Science and Technology
Volume	105
Issue number	1
DOIs	https://doi.org/10.1002/ejlt.200390005
Publication status	Published - 2003
Externally published	Yes

Keywords

13S-HODE
Sharpless epoxidation

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10.1002/ejlt.200390005

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

abstract = "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.",

keywords = "13S-HODE, Sharpless epoxidation",

author = "Omar, \{Muhammad Nor\} and Moynihan, \{Humphrey A.\} and Hamilton, \{Richard J.\}",

year = "2003",

doi = "10.1002/ejlt.200390005",

language = "English",

volume = "105",

pages = "43--44",

journal = "European Journal of Lipid Science and Technology",

issn = "1438-7697",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Asymmetric Sharpless epoxidation of 13S-hydroxy-9Z, 11E-octadecadienoic acid (13S-HODE)

AU - Omar, Muhammad Nor

AU - Moynihan, Humphrey A.

AU - Hamilton, Richard J.

PY - 2003

Y1 - 2003

N2 - 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.

AB - 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.

KW - 13S-HODE

KW - Sharpless epoxidation

UR - https://www.scopus.com/pages/publications/0037280514

U2 - 10.1002/ejlt.200390005

DO - 10.1002/ejlt.200390005

M3 - Article

AN - SCOPUS:0037280514

SN - 1438-7697

VL - 105

SP - 43

EP - 44

JO - European Journal of Lipid Science and Technology

JF - European Journal of Lipid Science and Technology

IS - 1

ER -

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

Abstract

Keywords

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