6533b7d5fe1ef96bd126511a

RESEARCH PRODUCT

Tandem asymmetric Michael reaction-intramolecular Michael addition. An easy entry to chiral fluorinated 1,4-dihydropyridines.

Silvia CatalanAntonio Simón-fuentesMaría Sánchez-rosellóSantos FusteroCarlos Del Pozo

subject

chemistry.chemical_classificationModels MolecularDihydropyridinesTandemHydrocarbons FluorinatedMolecular StructureChemistryOrganic ChemistryDiastereomerSulfoxideStereoisomerismBiochemistryCombinatorial chemistryCatalysischemistry.chemical_compoundIntramolecular forceAlkynesMichael reactionOrganic chemistryCombinatorial Chemistry TechniquesPhysical and Theoretical ChemistryAlkyl

description

A novel one-pot tandem asymmetric Hantzsch-type process has been employed to generate fluorinated 1,4-dihydropyridines (1,4-DHPs) as single diastereoisomers. It involves the condensation of (R)-(+)-allyl p-tolyl sulfoxide, fluorinated nitriles, and alkyl propiolates, giving access to a new family of enantiomerically pure fluorine-containing 1,4-DHPs.

10.1021/ol101318thttps://pubmed.ncbi.nlm.nih.gov/20617822