Enantioselective Synthesis of Planar Chiral Fluoroalkenes via Kinetic Resolution of gem-Difluorovinylferrocenes
Shuchen Lei , Hao Wu , Dachang Bai
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (22) : 2943 -2950.
Enantioselective Synthesis of Planar Chiral Fluoroalkenes via Kinetic Resolution of gem-Difluorovinylferrocenes
Planar organofluorine compounds are highly sought-after structural motifs. Herein, we present an enantioselective strategy for the synthesis of planar chiral fluoroalkenes via kinetic resolution of gem-difluorovinylferrocenes by copper-catalyzed hydrodefluorination in the presence of a base and diboron. This method was successfully applied to provide a diverse range of planar chiral gem-difluoroalkenes and Z-monofluoroalkenes with excellent regio-, stereo- and enantioselectivity. The resulting enantioenriched planar chiral fluoroalkenes could undergo various enantioretaining transformations, broadening their synthetic utility. Furthermore, density functional theory (DFT) calculations provide mechanistic insights into the origin of enantioselectivity, enhancing the understanding of this transformation.
Planar chiral fluoroalkenes / Kinetic resolution / Copper / Hydrodefluorination / Ferrocenes
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
/
| 〈 |
|
〉 |
PDF
