• Title/Summary/Keyword: ${\alpha}$-Cyanoalkylphosphonates

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Reactions of Phosphites with Nitroalkene Derivatives: Syntheses of $\beta$-Keto Phosphonates and $\alpha$-Cyanoalkylphosphonates

  • 김대영;오동영
    • Bulletin of the Korean Chemical Society
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    • v.18 no.9
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    • pp.994-998
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    • 1997
  • The addition of phosphite derivatives 1 to nitroalkenes 2 afforded α-phosphoryl nitronates which, on treatment MCPBA, were converted β-keto phosphonates 3. A versatile reaction conditions to generate α-phosphoryl nitronates were examined. α-Cyanoalkylphosphonates 6 were prepared from the diethyl trimethylsilyl phosphite (DTSP) 1c with nitroalkenes 2 and followed by reduction.

Catalytic Enantioselective Fluorination Reactions of α-Cyano Acetates and α-Cyanophosphonates Using Chiral Palladium Complexes

  • Kim, Sun-Mi;Kang, Young-Ku;Cho, Min-Je;Mang, Joo-Yang;Kim, Dae-Young
    • Bulletin of the Korean Chemical Society
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    • v.28 no.12
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    • pp.2435-2441
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    • 2007
  • The catalytic enantioselective electrophilic fluorinations of active methane compounds promoted chiral palladium complexes have been developed. Treatment of α-cyano acetates and α-cyanoalkylphosphonates with N-fluorobenzenesulfonimide as the fluorine source under mild reaction conditions afforded the corresponding α-cyano-α-fluorinated adducts in high yields with excellent enantiomeric excesses (up to 99% ee). These reactions can be conducted in alcoholic solvents without any precaution to exclude water and moisture.