ArticleNature communications2021
Near quantitative synthesis of urea macrocycles enabled by bulky N-substituent.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 28 citations in OpenAlex.
- Isodesmic Supramolecular Assembly of Phenylethynylene Bis-Urea Macrocycles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Macrocyclization of native peptides through (thio)urea crosslinking of two amines.Nature communications · 2026Article
- Conversion of all polyester units to amines: Ruthenium-catalyzed, acid-assisted hydrogenative amination.Science advances · 2026Article
- A one-pot strategy for the synthesis and functionalization of hyperbranched polytriazoles.Designed monomers and polymers · 2025Article
- Nanocomposites of Poly(Polymers · 2024Article
- Dynamic mechanostereochemical switching of a co-conformationally flexible [2]catenane controlled by specific ionic guests.Nature communications · 2024Article
- Continuous Flow Processes as an Enabling Tool for the Synthesis of Constrained Pseudopeptidic Macrocycles.The Journal of organic chemistry · 2022Article
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Authors and funding
11 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Macrocycles are unique molecular structures extensively used in the design of catalysts, therapeutics and supramolecular assemblies. Among all reactions reported to date, systems that can produce macrocycles in high yield under high reaction concentrations are rare. Here we report the use of dynamic hindered urea bond (HUB) for the construction of urea macrocycles with very high efficiency. Mixing of equal molar diisocyanate and hindered diamine leads to formation of macrocycles with discrete structures in nearly quantitative yields under high concentration of reactants. The bulky N-tert-butyl plays key roles to facilitate the formation of macrocycles, providing not only the kinetic control due to the formation of the cyclization-promoting cis C = O/tert-butyl conformation, but also possibly the thermodynamic stabilization of macrocycles with weak association interactions. The bulky N-tert-butyl can be readily removed by acid to eliminate the dynamicity of HUB and stabilize the macrocycle structures.
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Registered trials
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