Regioselective Functionalization of 3‐Hydroxy‐pyridine Carboxylates by Neighboring Group Assistance |
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Authors: | K Philip Wojtas Dr Jin‐Yong Lu Daniel Krahn Prof Dr Hans‐Dieter Arndt |
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Institution: | 1. http://www.arndtgroup.uni‐jena.de;2. Friedrich-Schiller-Universit?t, Institut für Organische Chemie und Makromolekulare Chemie, Jena, Germany |
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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. |
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Keywords: | amides neighboring-group effects regioselectivity scandium transesterification |
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