Journal ArticleDOI
Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to Diazo Groups in Diazido and Triazido Compounds
TLDR
Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated and the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds is reported.Abstract:
This paper reports on the selective conversion of alkyl azido groups at the carbonyl α-position to diazo compounds. Through β-elimination of dinitrogen, followed by hydrazone formation/decomposition, α-azidocarbonyl moieties were transformed into α-diazo carbonyl groups in one step. As these reaction conditions do not involve aryl or general alkyl azides, site-selective conversions of di- and triazides were achieved. Through this method, the successive site-selective conjugation of the triazido molecule with three different components is demonstrated.read more
Citations
More filters
Journal ArticleDOI
The Staudinger Ligation
TL;DR: The Staudinger reaction has been used especially in chemical biology for peptide/protein synthesis, posttranslational modifications, and DNA labeling, and it can be used for cell-surface engineering, development of microarrays, and drug delivery systems.
Journal ArticleDOI
Copper-Catalyzed Cascade Cyclization Reactions of Diazo Compounds with tert-Butyl Nitrite and Alkynes: One-Pot Synthesis of Isoxazoles.
TL;DR: A novel copper-catalyzed [3 + 2] cycloaddition reaction of alkynes with nitrile oxides generated in situ from the coupling reaction of copper carbene and nitroso radical has been developed and a catalytic cycle (CuI-CuII-Cu0-CuI) for this cascade cyclization reaction is proposed.
Journal ArticleDOI
Chemo- and Enantioselective Oxidative α-Azidation of Carbonyl Compounds
TL;DR: The enantioselective α-azidation of 1,3-dicarbonyls is achieved, as the first successful example of enantiOSElective intermolecular oxidative coupling using chiral hypoiodite catalysis.
Journal ArticleDOI
Sequential conjugation methods based on triazole formation and related reactions using azides.
TL;DR: This review highlights recent transformations involving selective triazole formation, allowing the efficient preparation of unsymmetric bis- and tris(triazole)s using diverse platform molecules.
Journal ArticleDOI
Site-selective conversion of azido groups at carbonyl α-positions into oxime groups leading triazide to a triple click conjugation scaffold.
TL;DR: With this method and diazo conversion, a triazido molecule was transformed into a triple click conjugation scaffold allowing one-pot four-component coupling.
References
More filters
Journal ArticleDOI
Cu-catalyzed azide-alkyne cycloaddition.
TL;DR: The basis for the unique properties and rate enhancement for triazole formation under Cu(1) catalysis should be found in the high ∆G of the reaction in combination with the low character of polarity of the dipole of the noncatalyzed thermal reaction, which leads to a considerable activation barrier.
Journal ArticleDOI
A Strain-Promoted [3 + 2] Azide−Alkyne Cycloaddition for Covalent Modification of Biomolecules in Living Systems
TL;DR: A strain-promoted [3 + 2] cycloaddition between cyclooctynes and azides that proceeds under physiological conditions without the need for a catalyst was demonstrated by selective modification of biomolecules in vitro and on living cells, with no apparent toxicity.
Journal ArticleDOI
Cell Surface Engineering by a Modified Staudinger Reaction
Eliana Saxon,Carolyn R. Bertozzi +1 more
TL;DR: A chemical transformation that permits the selective formation of covalent adducts among richly functionalized biopolymers within a cellular context is presented and should permit its execution within a cell's interior, offering new possibilities for probing intracellular interactions.
Journal ArticleDOI
Modern Organic Synthesis with α-Diazocarbonyl Compounds
TL;DR: This work aims to demonstrate the efforts towards in-situ applicability of EMMARM, which aims to provide real-time information about the physical properties of EMTs and their applications in the context of drug discovery and development.
Journal ArticleDOI
Recent studies on the reactions of α-diazocarbonyl compounds
Zhenhua Zhang,Jianbo Wang +1 more
TL;DR: New developments of various reactions of α-diazocarbonyl compounds have been reviewed in this article, which primarily focuses on the literatures published since 2003, focusing on the literature published in 2003.