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Karl Anker Jørgensen

Novel Organocatalytic Activation of Unmodified Morita-Baylis-Hillman Alcohols for the Synthesis of Bicyclic alpha-Alkylidene-Ketones

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  • Julian Stiller, Denmark
  • Dorota Kowalczyk, Lodz Univ Technol, Technical University Lodz, Inst Organ Chem, Dept Chem, Unknown
  • Hao Jiang, Denmark
  • Karl Anker Jorgensen
  • Lukasz Karol Albrecht, Lodz Univ Technol, Technical University Lodz, Inst Organ Chem, Dept Chem
The organocatalytic activation of Morita-Baylis-Hillman alcohols via H-bonding-iminium-ion formation is demonstrated for the first time. This activation strategy enables the Morita-Baylis-Hillman alcohols to undergo a formal S(N)2' reaction. In combination with the well-established enamine reactivity, this creates a new reactivity pattern. The application of this new activation mode for the synthesis of bicyclic alpha-alkylidene-ketones is demonstrated. The developed reaction sequence proceeds efficiently affording nature-inspired target products with four contiguous stereogenic centers in a highly stereoselective manner.
Original languageEnglish
JournalChemistry: A European Journal
Volume20
Issue41
Pages (from-to)13108-13112
Number of pages5
ISSN0947-6539
DOIs
Publication statusPublished - 6 Oct 2014

    Research areas

  • activation strategies, alpha-alkylidene-ketones, asymmetric synthesis, Morita-Baylis-Hillman adducts, organocatalysis, HIGHLY ENANTIOSELECTIVE EPOXIDATION, MULTIPLE STEREOCENTERS, OXINDOLES, CATALYSIS, FUNCTIONALIZATION, METHYLENOMYCINS, CONSTRUCTION, ANTIBIOTICS, ALKYLATION, ALDEHYDES

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