Synthesis of β-CF<sub>3</sub> β-Amino Esters with an Indane Backbone by Rhenium-Catalyzed [3+2] Annulation
Tingjun Hu, Yuanqing Xu, Saisai Zhang, Heng‐Ying Xiong, Guangwu Zhang
Abstract
The [3+2] annulation of trifluoromethylated ketimines with acrylates has been enabled by rhenium-catalyzed C–H activation, delivering a variety of β-CF3 β-amino esters. The reaction has exhibited broad substrate generality regarding aromatic CF3-ketimines and acrylates, the ability for gram scale synthesis, and facile derivation of the annulation products. The transformation is one of the few examples in which challenging sp2 C–H bonds of CF3-ketimines have been functionalized. The rapid assembly of biologically important fluorinated β-amino esters by this strategy will benefit the related studies and inspire a new approach for fluorinated motif synthesis.
Topics & Concepts
IndaneAnnulationChemistryRheniumCatalysisNaphthaleneStereochemistryCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalytic C–H Functionalization MethodsFluorine in Organic ChemistryCyclopropane Reaction Mechanisms