480997-20-4Relevant articles and documents
Stereoselective synthesis of 1,2- and 1,4-dihydropyridines by using cation-π interaction as a conformation-controlling tool
Yamada, Shinji,Saitoh, Momoe,Misono, Tomoko
, p. 5853 - 5857 (2002)
Selective shielding of one side of the pyridinium face by way of intramolecular cation-π complex formation enabled nucleophiles to attack the pyridinium ring from the non-shielded side. As a result, 1,2- and 1,4-dihydropyridines were formed in good stereoselectivities. 1H NMR analysis and ab initio calculations at the RHF/3-21G* level supported the existence of cation-π interaction between the pyridinium and the aromatic ring of the chiral auxiliary.