Atroposelective Three‐Component Coupling of Cyclic Diaryliodoniums and Sodium Cyanate Enabled by the Dual‐Role of Phenol
Shan Yang, Tianze Zheng, Longhui Duan, Xiaoping Xue, Zhenhua Gu
Abstract
A copper-catalyzed atroposelective ring-opening reaction of cyclic diaryliodoniums, sodium cyanate (NaOCN) and phenols is reported. The reaction chemoselectively affords axially chiral carbamates by sequential coupling of cyclic diaryliodonium and NaOCN, followed by phenol. Mechanistic investigations revealed that phenol is not only a reagent to trap highly active intermediate isocyanates, but it also activates the copper catalyst as a standby ligand. The carbamates were readily transformed into highly functionalized urea derivatives within a simple nucleophilic substitution reaction.
Topics & Concepts
ChemistryPhenolReagentCyanateCatalysisPhenolsNucleophileCombinatorial chemistryLigand (biochemistry)CopperOrganic chemistryBiochemistryReceptorAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralitySphingolipid Metabolism and Signaling