Synergistic Pd/Cu catalysis for stereoselective allylation of vinylethylene carbonates with glycine iminoesters: Enantioselective access to diverse trisubstituted allylic amino acid derivatives
Miaolin Ke, Zhigang Liu, Ke Zhang, Sheng Zuo, Fen‐Er Chen
Abstract
We reported a synergistic Pd/Cu catalyzed enantioselective decarboxylative allylation of vinylethylene carbonates with glycine iminoesters, which provides facile access to non-proteinogenic diverse trisubstituted allylic amino acid derivatives in high yields, exclusive regioselectivities and excellent stereoselectivities. This reaction tolerates a wide range of γ and β-aryl substituted vinylethylene carbonates with either electron-donating or electron-withdrawing groups. Significantly, this method was proven to be sufficient in the gram scale synthesis of chiral trisubstituted allylic amino acid while retaining the enantioselectivity and geometric control.
Topics & Concepts
Allylic rearrangementEnantioselective synthesisStereoselectivityGlycineChemistryArylCatalysisAmino acidCombinatorial chemistryStereoisomerismStereochemistryOrganic chemistryAlkylBiochemistryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods