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Telescoped Enolate Arylation/HWE Procedure for the Preparation of 3-Alkenyl-Oxindoles: The First Synthesis of Soulieotine

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JournalEuropean Journal of Organic Chemistry
DatePublished - Jun 2009
Issue number18
Number of pages6
Pages (from-to)2947-2952
Original languageEnglish

Abstract

A telescoped sequence involving palladium-catalysed intramolecular enolate arylation followed by an in situ HWE olefination has been developed to provide rapid access to 3-alkenyl-oxindoles. This "one-pot" process, which is greatly accelerated by microwave irradiation, proceeds with low loadings of palladium(II) acetate (0.2-1.0 mol-%), and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes as well as formaldehyde. In addition, further elaboration of the formaldehyde adducts are described. The applicability of the process has been established by carrying out the first synthesis of Soulieotine, a constituent of a traditional Chinese medicine. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

    Research areas

  • Horner-Wadsworth-Emmons olefination, Phosphonates, Enolate arylation, Palladium catalysis, Oxindoles, Telescoped reactions, INTRAMOLECULAR ALPHA-ARYLATION, PALLADIUM-CATALYZED SYNTHESIS, POLYSUBSTITUTED INDOLES, H FUNCTIONALIZATION, CASCADE REACTIONS, CARBENE LIGANDS, OXINDOLES, CYCLOADDITION, COMPLEXES, AMIDES

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