Copper-Catalyzed\nAsymmetric Nucleophilic Substitutions\nof TsSCF<sub>3</sub>: Synthesis of Chiral SCF<sub>3</sub>‑Containing\nCompounds

By employing electrophilic TsSCF<sub>3</sub> as an efficient\nSCF<sub>3</sub> source, we reported Cu/<b>SOP</b> (chiral sulfoxide-phosphine\nligand)-catalyzed enantioselective nucleophilic substitutions. Under\nthis protocol, α-pyridyl-α-fluoro esters as latent carbon\nnucleophiles, compounds containing a C-SCF<sub>3</sub> stereocenter\nalong with azacycles and fluorine atoms, were obtained in good yields\nand enantioselectivities under mild conditions (up to 68% yield, 92%\nee).

Publication Details

Journal
Figshare
Published
2024-12-02
DOI
https://doi.org/10.1021/acs.joc.4c01803.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Copper-Catalyzed\nAsymmetric Nucleophilic Substitutions\nof TsSCF3: Synthesis of Chiral SCF3‑Containing\nCompounds

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Fluorine in Organic Chemistry
article

Copper-Catalyzed\nAsymmetric Nucleophilic Substitutions\nof TsSCF3: Synthesis of Chiral SCF3‑Containing\nCompounds

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Abstract

By employing electrophilic TsSCF<sub>3</sub> as an efficient\nSCF<sub>3</sub> source, we reported Cu/<b>SOP</b> (chiral sulfoxide-phosphine\nligand)-catalyzed enantioselective nucleophilic substitutions. Under\nthis protocol, α-pyridyl-α-fluoro esters as latent carbon\nnucleophiles, compounds containing a C-SCF<sub>3</sub> stereocenter\nalong with azacycles and fluorine atoms, were obtained in good yields\nand enantioselectivities under mild conditions (up to 68% yield, 92%\nee).

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Fluorine in Organic Chemistry
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Copper-Catalyzed\nAsymmetric Nucleophilic Substitutions\nof TsSCF<sub>3</sub>: Synthesis of Chiral SCF<sub>3</sub>‑Containing\nCompounds · Figshare (2024) | TGRS Research Map | TGRS