Synthesis of N–N Axially Chiral Pyrrolyl-oxoisoindolin via Isothiourea-Catalyzed Acylative Dynamic Kinetic Resolution
Tongtong Wang, Jun Cao, Xin Li
Abstract
The development of methods for the asymmetric synthesis of N-N axial chirality remains elusive and challenging. Here, we disclose a method for the construction of N-N axially chiral pyrrolyl-oxoisoindolins along with central chirality via the isothiourea (ITU)-catalyzed acylative dynamic kinetic resolution (DKR). Axial chirality was introduced into the acylative DKR of hemiaminals for the first time. This protocol features mild conditions with excellent yields and enantioselectivities.
Topics & Concepts
Kinetic resolutionChemistryCatalysisAxial symmetryKinetic energyResolution (logic)Combinatorial chemistryEnantioselective synthesisComputational chemistryStereochemistryOrganic chemistryPhysicsClassical mechanicsArtificial intelligenceComputer scienceQuantum mechanicsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAlkaloids: synthesis and pharmacology