Cu-Catalyzed Switchable Asymmetric Defluoroalkylation and [3 + 2] Cycloaddition of Trifluoropropene
Hongyi Wang1, Juan Li2, Lingzi Peng1
1Hefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, China.
Abstract:
Chiral fluorinated amino esters and pyrrolidines are privileged scaffolds in synthetic chemistry and exhibit unique biological properties. We report the facile preparation of these compounds through copper-catalyzed switchable defluoroalkylation and [3 + 2] cycloaddition of trifluoropropene in an asymmetric fashion. The choice of solvent and chiral ligand was crucial for the efficient transformation and exquisite chemoselectivity pattern from identical starting materials that rapidly and reliably incorporate gem-difluoroalkene and trifluoromethyl (CF3) motifs to generate a diverse range of enantioenriched fluorinated building blocks in good to excellent yields with high asymmetric induction.
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