Asymmetric α-Allylation of <i>N</i>-Unprotected Amino Acid Esters with 1,3-Disubstituted Allyl Acetates Enabled by Chiral-Aldehyde/Palladium Catalysis
Zhou Qing, Zhi-Wei Yin, Zhu‐Lian Wu, Tian Cai, Wei Wen, Yanmin Huang, Qi‐Xiang Guo
Abstract
A chiral aldehyde/palladium catalysis-enabled asymmetric α-allylation of NH 2 -unprotected amino acid esters with 1,3-disubstituted allyl acetates is described in this work. With the utilization of different chiral phosphine ligands, both the anti- and syn- selective allylation reactions are achieved enantioselectively. A series of α,α-disubstituted amino acid esters bearing two adjacent chiral centers are produced in moderate-to-excellent yields, diastereoselectivities, and enantioselectivities.
Topics & Concepts
ChemistryAldehydePalladiumCatalysisPhosphineAmino acidOrganic chemistryAsymmetric hydrogenationCombinatorial chemistryEnantioselective synthesisBiochemistryAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods