55332-35-9Relevant academic research and scientific papers
Enantioselective Hydrogenation of Tetrasubstituted α,β-Unsaturated Carboxylic Acids Enabled by Cobalt(II) Catalysis: Scope and Mechanistic Insights
Du, Xiaoyong,Xiao, Ye,Yang, Yuhong,Duan, Ya-Nan,Li, Fangfang,Hu, Qi,Chung, Lung Wa,Chen, Gen-Qiang,Zhang, Xumu
supporting information, p. 11384 - 11390 (2021/04/09)
Chiral carboxylic acids are important compounds because of their prevalence in pharmaceuticals, natural products and agrochemicals. Asymmetric hydrogenation of α,β-unsaturated carboxylic acids has been widely recognized as one of the most efficient synthetic approaches to afford such compounds. Although related asymmetric hydrogenation of di- and trisubstituted unsaturated acids with noble metals is well established, asymmetric hydrogenation of challenging tetrasubstituted α,β-unsaturated carboxylic acids is rarely reported. We demonstrate enantioselective hydrogenation of cyclic and acyclic tetrasubstituted α,β-unsaturated carboxylic acids via cobalt(II) catalysis. This protocol showed broad substrate scope and gave chiral carboxylic acids in good yields with excellent enantiocontrol (up to 98 % yield and 99 % ee). Combined experimental and computational mechanistic studies support a CoII catalytic cycle involving migratory insertion and σ-bond metathesis processes. DFT calculations reveal that enantioselectivity may originate from the steric effect between the phenyl groups of the ligand and the substrate.
Synthesis of Optically Active α-Isopropyl-4-substituted Phenylacetic Acids by Asymmetric Hydrogenation
Takemoto, Ichiki,Kawamura, Norio,Kaminaka, Hiroshi
, p. 2071 - 2072 (2007/10/02)
Homogeneous hydrogenation of 2-phenyl-3-methyl-2-butenoic acid derivatives in the presence of a catalytic amount of such chiral phosphine-rhodium complexes as Rh/(R)-BINAP, Rh/(R)-, or (S)-Cy-BINAP, Rh/(R)-p-tolyl-BINAP, and Rh/(R)-p-methoxyphenyl-BINAP afforded the corresponding phenylacetic acid derivatives in high enantiomeric excesses and in quantitative chemical yields.The optically activa phenylacetic acid derivatives are useful intermediates of agrochemicals and pharmaceuticals.
