6533b7d1fe1ef96bd125cf44

RESEARCH PRODUCT

Enantioselective zinc-mediated conjugate alkynylation of saccharin-derived 1-aza-butadienes

Alvaro CastillaAmparo Sanz-marcoM. Carmen MuñozCarlos VilaGonzalo BlayJosé R. PedroDavid Sanz

subject

Molecular Conformationchemistry.chemical_elementZincConjugated systemCrystallography X-RayLigandsCatalysisStereocenterchemistry.chemical_compoundSaccharinCompostos orgànicsMaterials ChemistryChemistryArylChiral ligandMetals and AlloysEnantioselective synthesisStereoisomerismGeneral ChemistryDiethylzincCombinatorial chemistrySurfaces Coatings and FilmsElectronic Optical and Magnetic MaterialsZincCeramics and CompositesIminesQuímica orgànicaConjugate

description

The enantioselective 1,4-alkynylation of conjugated imines derived from saccharin with aryl- and alkyl-substituted terminal alkynes has been achieved. The reaction mediated by diethylzinc in the presence of a catalytic amount of a bis(hydroxy)malonamide chiral ligand provides the corresponding imines bearing a propargylic stereocenter with moderate yields and fair to excellent enantioselectivities.

https://doi.org/10.1039/d0cc04221h