COAP-Pd Catalyzed Asymmetric Allylic Alkylation of Azlactones with MBH Carbonates: Access to Unnatural α-Quaternary Stereogenic Glutamic Acid Derivatives
Sheng‐Suo Zhou, Xing‐Yun Sun, Wenkai Liu, Jiayu Song, Zheng Wang, Zheng‐Hang Qi, Xing‐Wang Wang
Abstract
A palladium-catalyzed regioselective and asymmetric allylic alkylation of azlactones with MBH carbonates has been developed with chiral oxalamide-phosphine ligands. The corresponding reaction afforded a range of optically active γ-arylidenyl glutamic acid derivatives bearing an α-chiral quaternary stereocenter in good yields with excellent linear regio- and high enantioselectivity. This protocol furnishes an alternative approach for the construction of enantio-enriched unnatural α-amino acid derivatives.
Topics & Concepts
StereocenterTsuji–Trost reactionRegioselectivityPhosphineChemistryAlkylationAllylic rearrangementCatalysisCombinatorial chemistryPalladiumStereochemistryOrganic chemistryEnantioselective synthesisAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisChemical Synthesis and Analysis