Site-specific hydrogen/deuterium exchange is an important method to access deuterated compounds for chemical and biological studies. Herein is reported the first method for the regioselective α-deuteration of enals and enones. The transformation features DO and AcOD as deuterium sources and amines as organocatalysts. The deuteration strategy is scalable and works on enals with a variety of substituted arene or heterocycle motifs as well as enones. The method has been applied to the synthesis of deuterated drug precursors.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.orglett.0c03839 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Cationic Polyhedral Chalcogenaboranes: Activation without breaking Wade's Rules.
Angew Chem Int Ed Engl
January 2025
University Pardubice Faculty of Chemical Technology: Univerzita Pardubice Fakulta Chemicko-Technologicka, Department of General and Inorganic Chemistry, CZECHIA.
Wade's rules are a well-established tool for the description of the geometry of inorganic clusters. Among others, they state that a decrease or increase in charge is always accompanied by a change in the number of skeletal electron pairs (SEPs). This work reports the synthesis of the first cationic chalcogenaboranes closo-[12-X-2-IPr-1-EB11H10]BF4 (X = H, I; E = S, Se 3a/b, 4a/b) featuring the same SEP count as their neutral precursors, EB11H11, but bearing a positive charge.
View Article and Find Full Text PDFMicrowave-assisted [3 + 2] cycloaddition reactions of dicyanoepoxides with benzylidene Meldrum's acids.
Org Biomol Chem
January 2025
Natural and Medical Sciences Research Center, University of Nizwa, P.O. Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Sultanate of Oman.
The [3 + 2] cycloaddition of dicyanoepoxides with benzylidene Meldrum's acid under microwave irradiation and solvent-free conditions was explored for the synthesis of trioxaspirodecanes. This method presents a highly diastereo- and regioselective route to spiro cycloadducts, delivering similar stereoselectivity to conventional reflux in toluene but with shorter reaction times and improved yields.
View Article and Find Full Text PDFThe Electrochemical Iodination of Electron-Deficient Arenes.
Angew Chem Int Ed Engl
January 2025
Institut für Chemie, Carl von Ossietzky Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26129, Oldenburg, Germany.
The iodination of electron-deficient arenes and heteroarenes is a long-standing problem in organic synthesis. Herein we describe the electrochemical iodination in nitromethane with BuNI as iodine source and supporting electrolyte under Lewis acid-free conditions in the presence of small amounts of chloride anions. The electrochemically generated reagent could be applied for the iodination of halogenated arenes, aromatic aldehydes, acids, esters, ketones, as well as nitroarenes to afford the products in good to excellent yields.
View Article and Find Full Text PDFLight-Driven Regioselective Deoxygenation of Carbohydrate Lactones for 2-Deoxy Sugar Precursor Synthesis.
Org Lett
January 2025
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw 01-224, Poland.
A sustainable method for the synthesis of 2-deoxy lactones as direct precursors to 2-deoxy sugars via regioselective UV-light-driven dealkyloxylation of carbohydrate-derived lactones is detailed. This catalyst- and additive-free protocol utilizes light irradiation, providing high step economy and functional group compatibility. This environmentally friendly and straightforward approach enhances the synthetic toolbox for 2-deoxy sugars, which is vital in numerous biologically active molecules and drug candidates.
View Article and Find Full Text PDFEnantioselective Pd- and Cu-Catalyzed Hydrofunctionalization of Methylenecyclopropanes via a Distal C-C Bond Cleavage.
Org Lett
January 2025
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165, China.
The enantioselective ring-opening reactions of methylenecyclopropanes (MCPs) involving C-C bond activation via oxidative addition of transition metals have been rarely reported. Here, we disclose a Pd/Cu-catalyzed enantio- and regioselective coupling between cyclic imino esters and MCPs to produce α-allylated 2-pyrrole derivatives. In this reaction, azomethine ylide formed by a chiral copper catalyst with ketimine ester would serve as a nucleophile to react with activated MCPs via palladium catalysis.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!