Counterion-Mediated Enantioconvergent Synthesis of Axially Chiral Medium Rings
Ji‐Yuan Du, Tudor Balan, Timothy D. W. Claridge, Martin D. Smith
Abstract
. We propose that the chiral ammonium salt differentiates between a complex and rapidly equilibrating mixture of enolate and rotational isomers, ultimately leading to highly enantioselective alkylative ring closure. This dynamic and enantioconvergent process offers an operationally simple approach to the synthesis of valuable chiral medium ring lactams for which there are few catalytic and enantioselective approaches.
Topics & Concepts
ChemistryEnantioselective synthesisEnantiomerIntramolecular forceConformational isomerismCounterionIminiumAlkylationStereochemistryChirality (physics)Ring (chemistry)Computational chemistryCombinatorial chemistryOrganic chemistryCatalysisMoleculeIonChiral symmetry breakingQuarkNambu–Jona-Lasinio modelQuantum mechanicsPhysicsAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis