Person: Berná Cánovas, José
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A Thiourea-based Rotaxane Catalyst: Nucleophilic Fluorination Phase-Transfer Process Unlocked by the Mechanical Bond
We report a five-component clipping approach using activated isophthaloyl-derived esters to synthesize an amide-based thiourea rotaxane. This method overcomes acyl chloride limitations with nucleophilic thiourea threads. The steric hindrance of the mechanical bond enables, for the first time, an interlocked thiourea as a hydrogen-bonding phase-transfer organocatalyst in nu-cleophilic fluorinations. This highlights how mechanical bonds expand thiourea catalysis to processes previously incompatible with conventional catalysts.
Dataset used for the article: Post-Synthetic Modifications of Amide-Enaminone-Based [2]Rotaxanes for the Stereocontrolled Synthesis of Functionalized β-Lactams
Post-Synthetic Modifications of Amide-Enaminone-Based [2]Rotaxanes for the Stereocontrolled Synthesis of Functionalized β-Lactams
Novel amido-enaminone threads serve as efficient templates for the assembly of hydrogen-bonded [2]rotaxanes, enabling versatile post-synthetic modifications. Benzyl groups on the amido moiety allow for diastereoselective intramolecular cyclizations, yielding interlocked β-lactams. The enaminone motif makes possible the stopper exchange while preserving the mechanical bond. Combining cyclization with one-pot stopper exchange and dethreading enables the stereoselective synthesis of highly functionalized non-interlocked lactams featuring a second heterocycle at their side chain via reactions with hydrazines or hydroxylamine