4.7 Article

Enantioselective Synthesis of 4-Substituted Dihydrocoumarins through a Zinc Bis(hydroxyamide)-Catalyzed Conjugate Addition of Terminal Alkynes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 6, Pages 1071-1076

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201201120

Keywords

alkynylation; asymmetric catalysis; N; O ligands; nucleophilic addition; oxygen heterocycles

Funding

  1. Ministerio de Economia y Competitividad (Gobierno de Espana)
  2. FEDER (European Union) [CTQ2009-13083]
  3. Generalitat Valenciana [ACOMP2012-212, ISIC2012/001]

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A new enantioselective catalyst for the conjugate addition of terminal alkynes has been developed. Terminal alkynes react with 3-alkoxycarbonylcoumarins in the presence of diethylzinc and bis(hydroxyamide) ligands to give chiral non-racemic dihydrocoumarins substituted with an alkynyl group on the C-4 position with good yields and enantiomeric excesses up to 95%.

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