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Selective and Multiple Functionalization of Pyridines and Alkaloids via Mg- and Zn-Organometallic Intermediates

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journal contribution
posted on 06.05.2011, 00:00 by Milica Jaric, Benjamin A. Haag, Sophia M. Manolikakes, Paul Knochel
Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF3·OEt2. A full pyridine functionalization of all five positions of the pyridine ring can be realized by using an appropriate combination of TMP bases in the presence or absence of BF3·OEt2.