Synthesis of Chiral Sulfoxides via Pd(II)-Catalyzed Enantioselective C–H Alkynylation/Kinetic Resolution of 2-(Arylsulfinyl)pyridines
Tao Zhou, Meng‐Xue Jiang, Pu‐Fan Qian, Qi‐Jun Yao, Xue-Tao Xu, Kun Zhang, Bing‐Feng Shi
Abstract
A Pd(II)-catalyzed enantioselective C–H alkynylation of 2-(arylsulfinyl)pyridines via kinetic resolution using cheap and commercially available l-pGlu-OH as a chiral ligand is reported. A wide range of 2-(arylsulfinyl)pyridines were compatible with this protocol, giving the alkynylation products and recovered sulfoxides in high yields with high enantioselectivities (up to 99% ee). Furthermore, the enantioenriched products can be easily transformed to several other types of chiral sulfoxide scaffolds with the retention of enantiopurity.
Topics & Concepts
ChemistryEnantioselective synthesisKinetic resolutionCatalysisAlkynylationSulfoxideLigand (biochemistry)Combinatorial chemistryChiral ligandStereochemistryMedicinal chemistryOrganic chemistryReceptorBiochemistryCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions