Asymmetric Construction of Carbon–Fluorine Quaternary Stereogenic Centers via Synergistic Pd/Cu Catalysis
Miaolin Ke, Xinzhi Li, Jiayi Zong, Bowen Wang, Jinying Zheng, Shujia Zhang, Jian-Ai Chen, Fen‐Er Chen
Abstract
We developed an asymmetric decarboxylative allylic alkylation of vinylethylene carbonates with α-fluoro pyridinyl acetates through a synergistic palladium/copper catalysis. This protocol provides chiral allylic alcohol with carbon-fluorine quaternary stereogenic centers in good yield with good enantioselectivities and excellent regioselectivities. The utility of this approach was further demonstrated via a gram-scale experiment and derivatizations of the product.
Topics & Concepts
StereocenterChemistryTsuji–Trost reactionAllylic rearrangementCatalysisYield (engineering)Enantioselective synthesisQuaternary carbonFluorinePalladiumAlcoholCombinatorial chemistryMedicinal chemistryOrganic chemistryMetallurgyMaterials scienceFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms