4.6 Article

α,β-Unsaturated Acyl Cyanides as New Bis-Electrophiles for Enantioselective Organocatalyzed Formal [3+3]Spiroannulation

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 2, Pages 410-415

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201303613

Keywords

domino reactions; enantioselectivity; glutarimides; organocatalysis; spiroannulation

Funding

  1. Agence Nationale pour la Recherche [ANR-11-BS07-0014]
  2. Centre National de la Recherche Scientifique (CNRS)
  3. COST Action [CM0905]
  4. Aix-Marseille Universite
  5. Agence Nationale de la Recherche (ANR) [ANR-11-BS07-0014] Funding Source: Agence Nationale de la Recherche (ANR)

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alpha, beta-Unsaturated acyl cyanides are key bis-electrophile substrates for successful domino enantioselective organocatalyzed Michael-intramolecular acylation domino sequences. This new reactivity has been applied to the synthesis of enantioenriched azaspiro[4,5] decanone ring systems by a formal [3+ 3] spiroannulation, constituting a rare example of synthesis of glutarimides in an optically active form.

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