Epoxidation of a conjugated linoleic acid isomer

Abstract

Epoxidation of a conjugated linoleic acid isomerEpoxidation of methyl (9Z,11E)-octadecadienoate (1) with various epoxidizing agents viz. m-chloroperoxybenzoic acid, dimethyl dioxirane, methyltrioxorhenium/hydrogen peroxide, potassium peroxomonosulfate (Oxone, 2KHSO 5 · KHSO 4 · K 2 SO 4 )/tetrahydrothiopyran-4-one, and Novozyme 435/hydrogen peroxide is described. The reactions furnished the corresponding mono-epoxy [methyl (11,12E)-epoxy-(9Z)-octadecenoate (2) and methyl (9,10Z)-epoxy-(11E)-octadecenoate (3)] and a mixture of diastereomers of syn-and anti-diepoxy-stearate [methyl (9,10Z;11,12E)-diepoxystearate (4a-4d)], which were identified by a combination of spectroscopic and spectrometric analyses.

Methyltrioxorhenium and its applications in olefin oxidation, metathesis and aldehyde olefination

“…The extension of epoxidation (10-50%) can be modulated by the amount of oxidant added, without significant change in the molecular weight of the polymer [96]. A conjugated linoleic acid isomer, methyl (9Z,11E)-octadecadienolate can also be successfully epoxidized with MTO/hydrogen peroxide [97]. Soybean oil can be oxidized by the MTO/CH 2 Cl 2 / H 2 O 2 catalytic biphasic system.…”

Regio- and Enantioselective Catalytic Monoepoxidation of Conjugated Dienes: Synthesis of Chiral Allylic cis-Epoxides

“…The application of the catalytic monoepoxidation method to the special case of 2,4-pentadiene-1-ols has been an area of long-standing interest . The resultant allylic epoxyols are versatile synthetic building blocks as well as key subunits, along with their chemically or enzymatically derived triols, in numerous bioactive natural products (Figure ) .…”