Details

Autor(en) / Beteiligte

• Prikhod'ko, Alexander
• Walter, Olaf
• Zevaco, Thomas A.
• Garcia-Rodriguez, Jaime
• Mouhtady, Omar
• Py, Sandrine

Titel

Synthesis of α-Amino Acids through Samarium(II) Iodide Promoted Reductive Coupling of Nitrones with CO2

Ist Teil von

• European journal of organic chemistry, 2012-07, Vol.2012 (20), p.3742-3746

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2012

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Several N‐benzylnitrones reacted with carbon dioxide in the presence of samarium(II) iodide leading to α‐amino acids as the products of reductive C–C coupling. The best selectivities were observed at a carbon dioxide pressure of 50 bar at ambient temperature. The influences of different functional groups in the nitrone backbone and of the coordinating additives to samarium(II) iodide on the product distribution were investigated. The racemic α‐amino acids were obtained in up to 70 % yield based on HPLC data. A novel approach to the synthesis ofα‐amino acids is disclosed, involvingC‐carboxylation of nitrones by gaseous CO2 under reductive coupling reaction conditions (SmI2, 0.1 M in THF) at ambient temperature and 50 bar of CO2 pressure.