122885-30-7Relevant academic research and scientific papers
One Stone Two Birds—Enantioselective Bimetallic Catalysis for α-Amino Acid Derivatives with an Allene Unit
Huo, Xiaohong,Ma, Shengming,Xiao, Junzhe,Xu, Haibo,Zhang, Wanbin
, p. 1958 - 1964 (2021)
A highly enantioselective 2,3-allenylation of acyclic and cyclic α-imino carboxylates via a synergistic bimetallic Pd/Cu catalysis with the same commercially available (R,Rp)-iPr-FOXAP (also as Phosferrox, (R,R)-[2-(4’-i-propyloxazolin-2’-yl)ferrocenyl]diphenyl phosphine) ligand for both metals affording optically active 2,3-butadienyl α-amino acid derivatives in high to excellent yields with excellent enantioselectivities has been developed. The synthetic versatility of this reaction has been demonstrated by gram-scale synthesis, a catalytic enantioselective synthesis of naturally occurring (S)-2-amino-4,5-hexadienoic acid A, and conversions to several useful chemicals, such as optically active α-amino acids, β-amino alcohols, potential chiral oxazoline ligands bearing an allenic moiety, and bicyclic ketone compounds. A mechanism involving the roles of two metals and the single chiral ligand has been extensively studied based on the isolation of key palladium pre-catalyst and control experiments.
