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Highly regio- and chemoselective palladium(0)-mediated allylic substitution of difunctional allylic halides with phenols

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JournalTetrahedron Letters
DatePublished - 8 Dec 2010
Issue number49
Volume51
Number of pages3
Pages (from-to)6378-6380
Original languageEnglish

Abstract

An efficient Pd(0)-mediated, base-assisted reaction of phenols with difunctionalised allylic halides results in the formation of coupled products in good yields. The reactions proceed with excellent stereo-, regio- and chemocontrol. An appropriately functionalised Weinreb amide, synthesised by this methodology, undergoes halogen-lithium exchange and subsequent intramolecular 1,2-carbonyl addition/elimination to give an advanced macrocyclic intermediate with potential use in the synthesis of likonide B. (C) 2010 Elsevier Ltd. All rights reserved.

    Research areas

  • Pd(0)-mediated reactions, Allylic substitution, Bifunctional allylic halides, Regioselective, Chemoselective, LIKONIDE-B, CATALYZED 1,4-DIACETOXYLATION, PROTEIN PRENYLATION, FARNESOL ANALOGS, THP ETHERS, LIGAND, (+/-)-SMENOCHROMENE-D, TRANSFERASE, METHYLATION, DIPHOSPHATE

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