Selective oxidations of methyl ricinoleate: diastereoselective epoxidation with titaniumIV catalysts

TA Foglia, PE Sonnet, A Nunez, RL Dudley

Index: Foglia; Sonnet; Nunez; Dudley JAOCS, Journal of the American Oil Chemists' Society, 1998 , vol. 75, # 5 p. 601 - 607

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Citation Number: 29

Abstract

Abstract Conditions were developed for the selective epoxidation of the double bond of methyl ricinoleate (1) with ethylmethyldioxirane (EMDO) to give the homoallylic epoxyalcohol, methyl (Z)-9, 10-oxido-12-hydroxyoctadecanoate (2) in high yields but in poor enantiomeric excess. The diastereomeric ratio for epoxyalcohol 2 was improved modestly when t-butyl-hydroperoxide, coupled with a titanium catalyst and ad-tartrate ligand, was ...