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Stereoselective Synthesis of Enamides by Pd-Catalyzed Hydroamidation of Electron Deficient Terminal Alkynes

Niranjan Panda* and Raghavender Mothkuri

*Department of Chemistry, National Institute of Technology, Rourkela-769008 Odisha, India, Email:

N. Panda, A. K. Jena, J. Org. Chem., 2012, 77, 9407-9412.

DOI: 10.1021/jo301772f

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A mild and operationally simple hydroamidation of electron-deficient terminal alkynes by amides in the presence of a Pd-catalyst enables a stereoselective synthesis of Z-enamides. Hydrogen bonding between the amido proton and carbonyl oxygen of ester group maybe provides the extra stability to the Z-isomer of an intermediate vinyl-palladium complex, which subsequently undergoes protodepalladation and leads to the Z-enamide selectively.

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Key Words

β-enamino esters, amides

ID: J42-Y2012-3420