Rhodium(III)-Catalyzed Kinetic Resolution of Racemic 1,6-Dienes via Asymmetric Borylative Cyclization
Junli Zhang, Dingding Gao, Yun‐Xuan Tan, Cheng‐Yu He, Pei-Ying Peng, Guo‐Qiang Lin, Qinghua Li, Ping Tian
Abstract
The rhodium(III)-catalyzed kinetic resolution of racemic nonactivated terminal alkene-tethered cyclohexadienones (1,6-dienes) has been developed with high to excellent selectivities (s up to 458) via asymmetric borylative cyclization, providing recovered cyclohexadienones and cis-hydrobenzofuranones with good to excellent yields and enantioselectivities (up to 99% ee). This reaction shows broad functional group tolerance and allows the further conversions of these two-type products to many optically active derivatives bearing multiple functionalities via Rh, Cu, Pd, and Ag catalysis.
Topics & Concepts
ChemistryKinetic resolutionRhodiumCatalysisAlkeneOptically activeFunctional groupCombinatorial chemistryEnantioselective synthesisStereochemistryMedicinal chemistryOrganic chemistryPolymerCatalytic C–H Functionalization MethodsSynthetic Organic Chemistry MethodsAsymmetric Synthesis and Catalysis