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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Synthesis of Acyclic Quaternary α-CF3-β-Oxo Carbonyls via Nucleophilic Substitution Induced by Single-Electron
Xiangyu Tan1, Pau Sarró1, Elies Molins2
1Department of Chemistry and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universitat Autónoma de Barcelona, 08193 Cerdanyola, Spain.
Abstract:
The development of efficient methods for the formation of quaternary centers in organic compounds has been a constant challenge in synthetic chemistry. Quaternary β-oxo esters are fundamental structures in the synthesis of natural products, pharmaceutical compounds, and other bioactive molecules. In this work, a direct and versatile approach to quaternary noncyclic β-oxo esters is reported using trifluoromethyl thianthrenium salt as highly reactive and selective reagent under mild conditions. Mechanistic investigations supported the operation via single-electron transfer-induced nucleophilic substitution.
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