Organocatalytic Enantioselective Arylation to Access Densely Aryl-Substituted P-Stereogenic Centers
Huilin Hu, Siqiang Fang, Xingjie Luo, Jiajia He, Jia‐Hong Wu, Zhishan Su, Zhipeng Xu, Tianli Wang
Abstract
Although methods for synthesizing chiral phosphorus scaffolds are available, the potential of this molecular chirality remains largely unexplored. Herein, we present a remote desymmetrization of prochiral biaryl phosphine oxides through an organocatalytic asymmetric arylation. This metal-free approach enables the efficient synthesis of a wide range of densely functionalized P(V)-stereogenic compounds with good to excellent yields and satisfactory enantioselectivities. Mechanistic studies reveal that hydrogen bonding and ion-pairing interactions are crucial for achieving precise stereocontrol in this transformation.
Topics & Concepts
StereocenterChemistryEnantioselective synthesisArylOrganocatalysisCatalysisStereochemistryCombinatorial chemistryOrganic chemistryAlkylAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and CatalysisSynthetic Organic Chemistry Methods