Enantioselective Catalytic Hantzsch Dihydropyridine Synthesis
Xinyue Hu, Long Chen, Hongye Li, Qifan Xu, Xiaohua Liu, Xiaoming Feng
Abstract
Optically enriched Hantzsch dihydropyridines bearing different ester groups were obtained through the asymmetric catalytic cascade reaction between 3-amino-2-butenoates and ( Z )-2-arylidene-3-oxobutanoates. The N, N ′-dioxide/Ni II or Nd III complex catalysts were disclosed to be efficient, furnishing a variety of the products, including drugs like nitrendipine, nimodipine, and felodipine, in high yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee). Two enantiomers of the products can be obtained readily via exchange of the ester group of the two reactants. In addition, axial chiral 4-arylpyridines were also afforded through an oxidation process.
Topics & Concepts
Enantioselective synthesisChemistryCatalysisYield (engineering)NitrendipineDihydropyridineNimodipineFelodipineEnantiomerOrganic chemistryCombinatorial chemistryCalciumMaterials scienceMedicineMetallurgyRadiologyBlood pressureAxial and Atropisomeric Chirality SynthesisMulticomponent Synthesis of HeterocyclesAsymmetric Synthesis and Catalysis