Enantioselective Synthesis of 1‐Aryl Benzo[5]helicenes Using BINOL‐Derived Cationic Phosphonites as Ancillary Ligands
Pablo Redero, Thierry Hartung, Jianwei Zhang, Leo D. M. Nicholls, Zichen Guo, Martín Simón, Christopher Golz, Manuel Alcarazo
Abstract
Abstract The synthesis of unprecedented BINOL‐derived cationic phosphonites is described. Through the use of these phosphanes as ancillary ligands in Au I catalysis, a highly regio‐ and enantioselective assembly of appropriately designed alkynes into 1‐(aryl)benzo[5]carbohelicenes is achieved. The modular synthesis of these ligands and the enhanced reactivity that they impart to Au I ‐centers after coordination have been found to be the key features that allow an optimization of the reaction conditions until the desired benzo[5]helicenes are obtained with high yield and enantioselectivity.
Topics & Concepts
Enantioselective synthesisCationic polymerizationChemistryArylCombinatorial chemistryYield (engineering)CatalysisReactivity (psychology)Organic chemistryMaterials scienceMetallurgyMedicinePathologyAlkylAlternative medicineSynthesis and Properties of Aromatic CompoundsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chirality