4.7 Article

Organocatalytic Asymmetric Synthesis of β-Aryl-β-isocyano Esters

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 11-12, Pages 2199-2210

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200140

Keywords

beta-aryl-beta-isocyano esters; imines; Mannich reaction; multicomponent reactions; organic catalysis; phase-transfer catalysis

Funding

  1. Fondazione San Paolo
  2. MIUR
  3. University of Genova

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The asymmetric addition of malonates to in situ generated N-formylimines of aromatic aldehydes was achieved under phase-transfer catalysis using Cinchona alkaloids-derived quaternary ammonium salts. The resulting beta-formamidomalonates have been efficiently converted into beta-aryl-beta-isocyano esters. Their utility in the multicomponent Ugi reaction with chiral cyclic imines has been demonstrated.

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