Cu-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of <i>N</i>-2,2,2-Trifluoroethylisatin Ketimines Enables the Desymmetrization of <i>N</i>-Arylmaleimides: Access to Enantioenriched F<sub>3</sub>C-Containing Octahydropyrrolo[3,4-<i>c</i>]pyrroles
Zhen‐Hua Wang, Jihong Liu, Yanping Zhang, Jian‐Qiang Zhao, Yong You, Ming‐Qiang Zhou, Wen‐Yong Han, Wei‐Cheng Yuan
Abstract
With a Cu(OTf)2/chiral ferrocenyl P,N-ligand complex as a catalyst, the enantioselective desymmetrization of N-arylmaleimides was successfully realized by taking advantage of the asymmetric 1,3-dipolar cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse F3C-containing octahydropyrrolo[3,4-c]pyrroles, bearing four contiguous carbon stereocenters and one stereogenic chiral C–N axial bond, were obtained with excellent results (≤99% yield, >20:1 dr, and 99% ee).
Topics & Concepts
StereocenterDesymmetrizationEnantioselective synthesisChemistryCycloadditionCatalysisYield (engineering)StereochemistryAsymmetric carbonLigand (biochemistry)Medicinal chemistryCombinatorial chemistryOrganic chemistryOptically activeReceptorMetallurgyBiochemistryMaterials scienceAsymmetric Synthesis and CatalysisFluorine in Organic ChemistryCyclopropane Reaction Mechanisms