Synthesis of<i>P</i>-Stereogenic Phosphinamides via Pd(II)-Catalyzed Enantioselective C–H Alkynylation
Tao Zhou, Lingjie Fan, Z.‐C. CHEN, Meng‐Xue Jiang, Pu‐Fan Qian, Xinquan Hu, Kun Zhang, Bing‐Feng Shi
Abstract
P -Stereogenic phosphinamides represent important structural elements in chiral organocatalysts and bioactive compounds. Herein, we report Pd(II)-catalyzed enantioselective C–H alkynylation using cheap commercially available l -pyroglutamic acid as a chiral ligand. A range of structurally diverse P -stereogenic phosphinamides was prepared in good yields with high enantioselectivities via desymmetrization and kinetic resolution. A tailor-made congested directing group, N -ethyl- N -(3-methylpyridin-2-yl)amino, was crucial for the reactivity.
Topics & Concepts
StereocenterEnantioselective synthesisChemistryAlkynylationCatalysisStereochemistryCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions