6533b7dbfe1ef96bd12709d5

RESEARCH PRODUCT

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

Amparo Sanz-marcoM. Carmen MuñozGonzalo BlayJosé R. Pedro

subject

Nucleophilic additionChemistryStereochemistryN O ligandsEnantioselective synthesischemistry.chemical_elementAlkynylationGeneral ChemistryZincCatalysisOxygen heterocyclesAlkynylationFISICA APLICADAAsymmetric catalysismedia_common.cataloged_instanceEuropean unionNucleophilic additionmedia_commonConjugate

description

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%.

https://doi.org/10.1002/adsc.201201120