Chiral Bis-8-Aryl-isoquinolineBis-alkylamine IronCatalysts for Asymmetric Oxidation Reactions

A novel class of bis-8-aryl-isoquinoline (^<b>Ar</b><b>iQ</b>) bis-alkylamine iron complexes, Fe^II(^<b>Ar</b><b>iQ₂dp</b>)­(OTf)₂ and Fe^II(^<b>Ar</b><b>iQ₂mc</b>)­(OTf)₂ (<b>dp</b> = dipyrrolidinyl or <b>mc</b> = <i>N</i>,<i>N</i>′-dimethylcyclohexyl-diamine), for asymmetric oxidation reactions is reported. The scalable divergent synthesis of 8-aryl-3-formylisoquinolines (<b>8</b>), the key intermediates in preparing these ligands, enables precise structural and electronic tuning around the metal center. The enantioselective epoxidation and hydroxy carbonylation of conjugated alkenes, mediated by the Fe^II(^{<b>3,5‑di‑CF₃</b>}<b>iQ₂dp</b>) catalyst with H₂O₂ as the oxidant, demonstrates the potential of these redox Fe^II[N₄] catalysts in inducing face selection in oxygen transfer transformations.