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A Hantzsch Amido Dihydropyridine as a Transfer Hydrogenation Reagent for α,β-Unsaturated Ketones

Scott A. Van Arman*, Austin J. Zimmet and Ian E. Murray

*Department of Chemistry, Franklin and Marshall College, Lancaster, Pennsylvania 17604-3003, United States, Email: scott.vanarmanfandm.edu

S. A. Van Arman, A. J. Zimmet, I. E. Murray, J. Org. Chem., 2016, 81, 3528-3532.

DOI: 10.1021/acs.joc.6b00041 (free Supporting Information)


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Abstract

Bis-methylamido Hantzsch dihydropyridine is an effective transfer hydrogenation reagent for the reduction of α,β-unsaturated ketones. Unreacted Hantzsch amide and the bis-methylamidopyridine byproduct are effectively removed by extraction in contrast to the commonly used Hantzsch diethyl ester. The reaction is more effective for conjugated aromatic substrates than for aliphatics.

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Key Words

reduction of enones, Hantzsch amides


ID: J42-Y2016