Work

Diastereoselective arylation of bis-lactim ethers catalyzed by N -coordinating ylide-functionalized phosphine (NYPhos)

Year: 2025

Type: article

Abstract: adYPhos effectively promote the coupling of aryl chlorides with a commercially available, valine-based Schöllkopf-reagent in 97% yield and a diastereoselectivity of 98 : 2. The arylglycines are accessible in high yields and enantiomeric excess by hydrolysis of the products. The correlation between diastereoselectivity and ligand properties identified the nature of the secondary metal-ligand interaction as a key factor in determining the selectivity of the arylation of bis-lactim ethers. Computational studies in combination with a quantitative structure-activity relationship analysis revealed that the rate-limiting step varies depending on the phosphine ligands used and that the secondary metal-ligand interaction determines diastereoselectivity.

Source: Chemical Science

DOI: 10.1039/d5sc02814k