Enantioselective arylation of 2-methylacetoacetates catalyzed by CuI/trans-4-hydroxy-L-proline at low reaction temperatures.

作者: Xiaoan Xie , Yu Chen , Dawei Ma

DOI: 10.1021/JA066991J

关键词: SubstituentCatalysisSolvent effectsLigandEnantioselective synthesisMoleculeStereoisomerismCoupling reactionMedicinal chemistryStereochemistryChemistry

摘要: CuI/trans-4-hydroxy-l-proline-catalyzed coupling reaction of 2-iodotrifluoroacetanilides with 2-methylacetoacetates took place at -45 degrees C to create alpha-aryl all-carbon quaternary centers enantioselectively. Up 93% ee was achieved when tert-butyl ester used. The combination ligand, ortho substituent (participation NHCOCF3), and solvent effects shown account for these unprecedentedly mild conditions.

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