ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
trans-Symmetric Dynamic Covalent Systems: Connected Transamination and Transimination Reactions.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Asymmetric Deoxy-Fluoroalkylation of Amides Enabled by Transimination.Organic letters · 2026Article
- Aromatic Dendrimers Bearing 2,4,6-Triphenyl-1,3,5-triazine Cores and Their Photocatalytic Performance.The Journal of organic chemistry · 2021Article
- Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.The Journal of organic chemistry · 2021Article
- Identification of Potent Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors Based on a Phenylimidazole Scaffold.ACS medicinal chemistry letters · 2018Article
- Dynamic Covalent Chemistry of Aldehyde Enamines: BiChemistry (Weinheim an der Bergstrasse, Germany) · 2017Article
- Antiparallel Dynamic Covalent Chemistries.Journal of the American Chemical Society · 2017Article
- Three-Component Reaction of Benzylamines, Diethyl Phosphite and Triethyl Orthoformate: Dependence of the Reaction Course on the Structural Features of the Substrates and Reaction Conditions.Molecules (Basel, Switzerland) · 2017Article
- Enzyme classification using complex dynamic hemithioacetal systems.Chemical communications (Cambridge, England) · 2016Article
Corrections and comments
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Authors and funding
3 authors.
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No grant is acknowledged in the PubMed record.
Abstract
The development of chemical transaminations as a new type of dynamic covalent reaction is described. The key 1,3-proton shift is under complete catalytic control and can be conducted orthogonally to, or simultaneous with, transimination in the presence of an amine to rapidly yield two-dimensional dynamic systems with a high degree of complexity evolution. The transamination-transimination systems are proven to be fully reversible, stable over several days, compatible with a range of functional groups, and highly tunable. Kinetic studies show transamination to be the rate-limiting reaction in the network. Furthermore, it was discovered that readily available quinuclidine is a highly potent catalyst for aldimine transaminations. This study demonstrates how connected dynamic reactions give rise to significantly larger systems than the unconnected counterparts, and shows how reversible isomerizations can be utilized as an effective diversity-generating element.
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Registered trials
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