6533b7d3fe1ef96bd1261690

RESEARCH PRODUCT

2-Alkenoyl Pyridine N-Oxides, Highly Efficient Dienophiles for the Enantioselective Cu(II)−Bis(oxazoline) Catalyzed Diels−Alder Reaction

Gonzalo BlayJosé R. PedroSantiago Barroso

subject

PyridinesCyclopentanesOxazolineAlkenesMedicinal chemistryBiochemistryCatalysisCatalysischemistry.chemical_compoundChalconeIsomerismPyridineOrganic chemistryReactivity (chemistry)Physical and Theoretical ChemistryOxazolesDiels–Alder reactionchemistry.chemical_classificationAza CompoundsMolecular StructureChemistryOrganic ChemistryEnantioselective synthesisGeneral MedicineBridged compoundsCopper

description

2-Alkenoyl pyridine N-oxides are introduced as a new kind of efficient dienophiles for the Cu(II)−bis(oxazoline) (BOX) catalyzed enantioselective Diels−Alder reaction affording higher reactivity and enantioselectivity (ee's up to 96%) than the corresponding nonoxidized 2-alkenoyl pyridines.

https://doi.org/10.1021/ol0705752