Diastereodivergent Parallel Kinetic Resolution of Racemic 2-Substituted Pyrrolidines via Iridium-Catalyzed C(<i>sp</i><sup>3</sup>)–H Borylation
Maosheng He, Liangjun Xie, Lili Chen, Senmiao Xu
Abstract
Chiral 2,5-disubstituted pyrrolidines are ubiquitous subunits in natural products, bioactive compounds, pharmaceuticals, and chiral catalysts. However, their asymmetric synthesis still presents a formidable challenge. We herein report a rare example of diastereodivergent parallel kinetic resolution of racemic 2-substituted pyrrolidines via C( sp 3 )–H borylation. A vast array of enantioenriched cis - and trans -2,5-disubstituted pyrrolidines were obtained with high enantioselectivities. The synthetic utility was demonstrated by downstream transformations, including the synthesis of optically active pyrrolidine 197B and cis -pyrrolidine 225H.
Topics & Concepts
BorylationIridiumCatalysisChemistryKinetic resolutionKinetic energyMedicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryEnantioselective synthesisPhysicsArylQuantum mechanicsAlkylCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions