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Access to Chiral Cyclic β‐Enaminones via Enantioselective Imine Condensation

Yaru Gao, Zhi‐Keng Lin, M.H Liu, Jiameng Deng, Tao Zhang, Bin‐Miao Yang, Yu Zhao

2025Angewandte Chemie International Edition8 citationsDOIOpen Access PDF

Abstract

We report herein an unprecedented catalytic enantioselective synthesis of cyclic β-enaminones from simple meso-1,3-diketones via chiral phosphoric acid-catalyzed desymmetrization through imine condensation. This transformation provides efficient access to a broad array of cyclic β-enaminones and acridinones bearing a remote β-stereogenic center, delivering products in excellent yields and enantioselectivities under mild conditions with a straightforward protocol. Furthermore, the resulting β-enaminones can undergo one-step derivatizations to furnish diverse enantioenriched carbo- and heterocycles, highlighting their high potential for applications in medicinal chemistry.

Topics & Concepts

Enantioselective synthesisDesymmetrizationImineStereocenterChemistryCombinatorial chemistryPhosphoric acidCatalysisCondensationOrganic chemistryThermodynamicsPhysicsSynthesis and Characterization of PyrrolesAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions