'Onium rings: Incorporation of the trivalent oxygen atom as a structural element within the tricyclic core of 1-3 imparts unprecedented stability to this "extraordinary" class of tertiary oxonium ions. Cation 1 is the least reactive and can be refluxed in water for 72 hours with no noticeable decomposition.
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http://dx.doi.org/10.1002/anie.200805417 | DOI Listing |
J Am Chem Soc
January 2025
State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China.
Taming highly enolizable aldehydes for catalytic asymmetric C-C coupling with nucleophiles remains an elusive challenge compared to widely explored simple alkyl or aryl aldehydes. Herein, we use ThDP-dependent enzymes to realize the direct C-C coupling of highly enolizable 2-phosphonate aldehydes with in situ-generated dynamically reversible nucleophiles (acyl anions). Unlike NHC-mediated reactions that yield complex mixtures of multiple adducts, our enzymatic process selectively produces biologically active β-hydroxy phosphonates with high yields (up to 95%) and excellent enantioselectivities (up to 99% ee).
View Article and Find Full Text PDFBeilstein J Org Chem
November 2024
Department of Chemistry and Chemical Biology, TU Dortmund University, Otto-Hahn-Straße 6, 44227 Dortmund, Germany.
J Am Chem Soc
November 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India.
The direct utilization of carbon dioxide as an ideal one-carbon source in value-added chemical synthesis has garnered significant attention from the standpoint of global sustainability. In this regard, the photo/electrochemical reduction of CO into useful fuels and chemical feedstocks could offer a great promise for the transition to a carbon-neutral economy. However, challenges in product selectivity continue to limit the practical application of these systems.
View Article and Find Full Text PDFJ Agric Food Chem
May 2024
Key Laboratory of Luminescence Analysis and Molecular Sensing (Southwest University), Ministry of Education, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, PR China.
With the booming development of food manufacturing, developing ideal analytical tools to precisely quantify food additives is highly sought after in the food science field. Herein, a new series of quinoline-derived multifunctional fluorescent probes has been synthesized. Bearing double reactive sites, these compounds display fluorescence response toward both bisulfite (HSO) and hypochlorous acid (HClO).
View Article and Find Full Text PDFOrg Lett
April 2024
FLAME-Lab, Flow Chemistry and Microreactor Technology Laboratory, Department of Pharmacy-Drug Sciences, University of Bari "A. Moro", Via E. Orabona 4, 70125, Bari, Italy.
The oxetane ring has evolved as a useful bioisostere for dimethyl and carbonyl groups for the improvement of physiochemical properties of drug candidates. Herein, we report the generation and utilization of highly unstable 3-oxetanyllithium as a hitherto unexplored nucleophile leveraging flash technology. A range of different electrophiles are suitable reaction partners in this protocol, and we demonstrate the utility of this protocol in late-stage pharmaceutical analogue synthesis.
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