Enantioselective Catalytic Hantzsch Dihydropyridine Synthesis

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/NiII or NdIII 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.

Automated summary

Optically enriched Hantzsch dihydropyridines with different ester groups were obtained through asymmetric catalytic cascade reaction. Efficient N,N'-dioxide/NiII or NdIII complex catalysts yielded a variety of 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 could be readily obtained via ester group exchange, and axial chiral 4-arylpyridines were also formed through oxidation.