Improved Condensation of 2-pyridyllithium Intermediates with Aldehydes: Application for the Synthesis of 2-(polyhydroxyalkyl)pyridines

Corinne      Comoy; Julien      Petrignet; Estelle      Banaszak; Anthony      Chartoire; Yves      Fort

doi:10.2174/157017809787003214

Abstract

The scope and the limitations of 3-chloro-2-pyridinyl lithium condensation to aldehydes were envisioned depending on metallation conditions or condensation time and temperatures. The procedure was applied to various aromatic, aliphatic or functionalized aldehydes to afford a new and efficient access to 2-(polyhydroxyalkyl)pyridines.

Keywords: Regioselective lithiation, [n-BuLi/LiDMAE] superbase, 2-pyridinyllithium, 2-(polyhydroxyalkyl)pyridines

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Letters in Organic Chemistry

Title: Improved Condensation of 2-pyridyllithium Intermediates with Aldehydes: Application for the Synthesis of 2-(polyhydroxyalkyl)pyridines

Volume: 6 Issue: 1

Author(s): Corinne Comoy, Julien Petrignet, Estelle Banaszak, Anthony Chartoire and Yves Fort

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Keywords: Regioselective lithiation, [n-BuLi/LiDMAE] superbase, 2-pyridinyllithium, 2-(polyhydroxyalkyl)pyridines

Abstract: The scope and the limitations of 3-chloro-2-pyridinyl lithium condensation to aldehydes were envisioned depending on metallation conditions or condensation time and temperatures. The procedure was applied to various aromatic, aliphatic or functionalized aldehydes to afford a new and efficient access to 2-(polyhydroxyalkyl)pyridines.

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Comoy Corinne, Petrignet Julien, Banaszak Estelle, Chartoire Anthony and Fort Yves, Improved Condensation of 2-pyridyllithium Intermediates with Aldehydes: Application for the Synthesis of 2-(polyhydroxyalkyl)pyridines, Letters in Organic Chemistry 2009; 6 (1) . https://dx.doi.org/10.2174/157017809787003214