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Published on: June 21, 2017
Synthesis of β-CF3 β-Amino Esters with an Indane Backbone by Rhenium-Catalyzed [3+2] Annulation
Tingjun Hu1, Yuanqing Xu1, Saisai Zhang1
1Institute of Organic Functional Molecules, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China.
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.
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