Highly Regioselective Synthesis of Ethyl 2-(N-Methylformate-1,4,5,6-tetrahydropyridin-2-yl) Acetate and Its Conversion into Corresponding (R)-Ethyl Homopepicolate by Asymmetric Hydrogenation

Iyad KaraméLaboratory of Organometallic Catalysis and Coordination Chemistry, Department of Chemistry, Lebanese University, Faculty of Sciences I, Haddath, Lebanon

Ghinwa Nemra-BaydounLaboratory of Organometallic Catalysis and Coordination Chemistry, Department of Chemistry, Lebanese University, Faculty of Sciences I, Haddath, Lebanon

Radwan AbdallahLaboratory of Organometallic Catalysis and Coordination Chemistry, Department of Chemistry, Lebanese University, Faculty of Sciences I, Haddath, Lebanon

Ali KanjLaboratory of Organometallic Catalysis and Coordination Chemistry, Department of Chemistry, Lebanese University, Faculty of Sciences I, Haddath, Lebanon

Armin BörnerLeibniz-Institut für Katalyse, Universität Rostock e.V., Rostock, Germany

Abstract

Ethyl 2-(N-methylformate-1,4,5,6-tetrahydropyridin-2-yl) acetate with endocyclic double bond was prepared with high regioselectivity and further reduced into (R)-N-protected homopipecolate with a good enantioselectivity using chiral ruthenium catalyst.

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ACKNOWLEDGMENT

We acknowledge financial support from Wirtschaftsministerium von Mecklenburg-Vorpommern.

Notes

Note. In ETOH (3 mL), Ru-Cat or Rh-Cat (2.5%), ligand/Ru 1.1, substrate/metal 40, 50 bars of H₂.

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Highly Regioselective Synthesis of Ethyl 2-(N-Methylformate-1,4,5,6-tetrahydropyridin-2-yl) Acetate and Its Conversion into Corresponding (R)-Ethyl Homopepicolate by Asymmetric Hydrogenation

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Highly Regioselective Synthesis of Ethyl 2-(N-Methylformate-1,4,5,6-tetrahydropyridin-2-yl) Acetate and Its Conversion into Corresponding (R)-Ethyl Homopepicolate by Asymmetric Hydrogenation

Abstract

ACKNOWLEDGMENT

Notes

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