Tetrahedron Letters p. 5853 - 5857 (2002)
Update date:2022-08-04
Topics:
Yamada, Shinji
Saitoh, Momoe
Misono, Tomoko
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.
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