Planar Chiral Rhodium Complex Based on the Tetrahydrofluorenyl Core for Enantioselective Catalysis
Vladimir B. Kharitonov, Evgeniya Podyacheva, Denis Chusov, Yulia V. Nelyubina, Dmitry V. Muratov, Dmitry A. Loginov
Abstract
A simple four-step route to a chiral tetrahydrofluorenyl rhodium catalyst from naturally occurring (−)-α-pinene was developed. Our approach does not use multistep and time-consuming procedures such as chiral HPLC or diastereomeric resolution. The key to success lies in the face-selective coordination of rhodium to the sterically hindered tetrahydrofluorenyl ligand, giving only one diastereomeric complex. This catalyst proved to be highly efficient for asymmetric C–H annulation of aryl hydroxamates with alkenes (yield up to 95%, 91% ee ) at low loading (up to 0.4 mol % based on Rh).
Topics & Concepts
Enantioselective synthesisRhodiumChemistryCatalysisCore (optical fiber)PlanarCombinatorial chemistryStereochemistryOrganic chemistryComputer scienceComputer graphics (images)TelecommunicationsAsymmetric Hydrogenation and CatalysisSurface Chemistry and CatalysisCatalytic C–H Functionalization Methods