Cyclization of interlocked fumaramides into β-lactams: experimental and computational mechanistic assessment of the key intercomponent proton transfer and the stereocontrolling active pocket
Alberto Martínez‐Cuezva, Aurelia Pastor, Marta Marín‐Luna, Carmen Diaz-Marin, Delia Bautista, Mateo Alajarı́n, José Berná
Abstract
-benzyl group of the thread by the amidate group of the macrocycle generated by the external base, (b) the polyamide macrocycle plays an important role not only as activating element but also as the stereodifferenciating factor responsible for the observed diastereoselection and (c) the higher flexibility of the adamantyl core speeds up the cyclization process in diadamantyl-derived rotaxanes.
Topics & Concepts
DeprotonationChemistryStereochemistryReactivity (psychology)Computational chemistryOrganic chemistryMedicinePathologyAlternative medicineIonSynthesis of β-Lactam CompoundsSynthesis and Catalytic ReactionsAsymmetric Synthesis and Catalysis