A novel highly enantio- and diastereoselective synthesis of vitamin E side-chain

作者: Yohei Matsueda , Shiqing Xu , Ei-ichi Negishi

DOI: 10.1016/J.TETLET.2014.12.081

关键词: AcetylationVitamin EProton NMREnantioselective synthesisSynthonStereochemistryChemistryOrganic chemistryIodideSide chainEnantiomer

摘要: Abstract A novel highly enantioselective (>99% ee) and diastereoselective (>98% de) method for the synthesis of chiral C 15 vitamin E side-chain 1 was developed. ZACA–lipase-catalyzed acetylation protocol to provide a key α,ω-dioxyfunctional 5 synthon 6 (⩾99% ee), two subsequent Cu-catalyzed alkyl–alkyl cross-coupling reactions enantiomerically pure iodide 4 were employed as steps. H NMR analysis MαNP ester found be convenient measuring enantiomeric purity .

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