Organic letters

Selective and multiple functionalization of pyridines and alkaloids via Mg-and Zn-organometallic intermediates

M Jaric, BA Haag, SM Manolikakes, P Knochel

Index: Jaric, Milica; Haag, Benjamin A.; Manolikakes, Sophia M.; Knochel, Paul Organic Letters, 2011 , vol. 13, # 9 p. 2306 - 2309

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Citation Number: 35

Abstract

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.