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Stereoselective synthesis of 1,2- and 1,4-dihydropyridines by using cation–π interaction as a conformation-controlling tool

✍ Scribed by Shinji Yamada; Momoe Saitoh; Tomoko Misono

Book ID: 104251559
Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 115 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)01166-8

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✦ Synopsis

Selective shielding of one side of the pyridinium face by way of intramolecular cation-p 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. 1 H NMR analysis and ab initio calculations at the RHF/3-21G* level supported the existence of cation-p interaction between the pyridinium and the aromatic ring of the chiral auxiliary.

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