Tackling <i>N</i>‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
Clemens K. Blasius, Niklas F. Heinrich, Vladislav Vasilenko, Lutz H. Gade
Abstract
A readily activated iron alkyl precatalyst effectively catalyzes the highly enantioselective hydroboration of N-alkyl imines. Employing a chiral bis(oxazolinylmethylidene)isoindoline pincer ligand, the asymmetric reduction of various acyclic N-alkyl imines provided the corresponding α-chiral amines in excellent yields and with up to >99 % ee. The applicability of this base metal catalytic system was further demonstrated with the synthesis of the pharmaceuticals Fendiline and Tecalcet.
Topics & Concepts
Enantioselective synthesisIsoindolineChemistryAlkylHydroborationCatalysisPincer ligandCombinatorial chemistryLigand (biochemistry)Organic chemistryPincer movementReceptorBiochemistryAsymmetric Hydrogenation and CatalysisOrganoboron and organosilicon chemistryAsymmetric Synthesis and Catalysis