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Catalytic Synthesis and Asymmetric Reduction of Pyridylglyoxylic Amides and Esters

Abstract : The preparation of 2‐pyridyl‐ and 4‐pyridylglyoxylic esters and amides in moderate to high yields via palladium‐catalyzed double carbonylation of 2‐iodo‐ and 4‐iodopyridines is reported. The effect of temperature, CO pressure, solvent, nature and concentration of nucleophile, nature of catalyst precursor, and substituents on iodopyridines has been investigated. The reduction of 4‐pyridylglyoxylate esters into the corresponding α‐hydroxy esters via ruthenium‐catalyzed asymmetric hydrogenation or using alpine‐borane proceeded in high yields but poor enantioselectivity. The results for the carbonylation and the hydrogenation catalytic processes are discussed in terms of electronic effects induced by the pyridyl ring.
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Contributor : Samuel Couve-Bonnaire <>
Submitted on : Thursday, November 28, 2019 - 2:03:13 PM
Last modification on : Friday, October 16, 2020 - 11:22:03 AM

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  • HAL Id : hal-02384514, version 1

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Samuel Couve-Bonnaire, Jean-François Carpentier, Andre Mortreux, Yves Castanet. Catalytic Synthesis and Asymmetric Reduction of Pyridylglyoxylic Amides and Esters. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2001, 343 (3), pp.289-298. ⟨hal-02384514⟩

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