title: Regioselective Functionalization of 3-Hydroxy-pyridine Carboxylates by Neighboring Group Assistance.
abstract: Regioselective hydrolysis, transesterification, and aminolysis of unactivated, highly substituted pyridine esters were realized under mild conditions by employing neighboring group assisted catalysis. Excellent yields were achieved without active removal of the alcohol byproduct. Regioselective aminolysis had a considerable substrate scope ([hetero]aryl, alkyl and amino acid). A mechanism involving assistance by the deprotonated phenolic OH-group is suggested for hydrolysis and transesterification.
authors: Friedrich-Schiller-Universität, Institut für Organische Chemie und Makromolekulare Chemie, Humboldtstraße 10, 07743, Jena, Germany.
authors: K Philip
authors: KP
authors: Wojtas
authors: Friedrich-Schiller-Universität, Institut für Organische Chemie und Makromolekulare Chemie, Humboldtstraße 10, 07743, Jena, Germany.
authors: Jin-Yong
authors: JY
authors: Lu
authors: Friedrich-Schiller-Universität, Institut für Organische Chemie und Makromolekulare Chemie, Humboldtstraße 10, 07743, Jena, Germany.
authors: Daniel
authors: D
authors: Krahn
authors: Friedrich-Schiller-Universität, Institut für Organische Chemie und Makromolekulare Chemie, Humboldtstraße 10, 07743, Jena, Germany. hd.arndt@uni-jena.de.
authors: Hans-Dieter
authors: HD
authors: Arndt
keywords: amides; neighboring-group effects; regioselectivity; scandium; transesterification