Kinetic Resolution of 2‐<i>N</i>‐Acylamido Tertiary Allylic Alcohols: Asymmetric Synthesis of Oxazolines
Yongkai Pan, Qian Jiang, Subramani Rajkumar, Chaofan Zhu, Jinglei Xie, Shaoze Yu, Yunrong Chen, Yu‐Peng He, Xiaoyu Yang
Abstract
Abstract A series of cyclohexyl‐fused SPINOL‐derived phosphoric acids (Cy‐SPA) have been developed to catalyze the kinetic resolution of 2‐ N ‐acylamido tertiary allylic alcohols, providing access to chiral oxazolines bearing C‐2 alkyl substituents with high enantioselectivities (with s ‐factors up to 153). Gram‐scale reaction with 1 mol% catalyst loading and transformations of the chiral products demonstrates the value of these methods. magnified image
Topics & Concepts
Kinetic resolutionChemistryAllylic rearrangementAlkylCatalysisEnantioselective synthesisKinetic energyOrganic chemistryResolution (logic)Medicinal chemistryStereochemistryPhysicsArtificial intelligenceComputer scienceQuantum mechanicsAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis