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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 34, Number 10
BKCSDE 34(10)
October 20, 2013 

A Versatile Synthesis of α-Keto (cyanomethylene)triphenylphosphorane Ylides from Alkyl Halides Utilizing a Noble Phenylsulfonyl Reagent
Kieseung Lee*, Chan-Yeon Hwang
α-Keto amide/ester, α-Keto (cyanomethylene)triphenylphosphorane ylide, Alkylation, Desulfonylation, Sodium amalgam
A noble phenylsulfonyl reagent 8 having α-oxo (cyanomethylene)triphenylphosphorane ylide subunit readily condensed with various alkyl halides under basic conditions to afford β-alkyl-α-oxo-β-phenylsulfonyl (cyanomethylene)triphenylphosphorane ylides 9 in excellent yields. These sulfonyl ylides 9 were then reductively desulfonylated with Na(Hg)/Na2HPO4 in the presence of methanol to provide α-keto (cyanomethylene)- triphenylphosphorane ylides 2' in good to excellent yields. Our new synthetic approach offers an expeditious access to various α-keto (cyanomethylene)triphenylphosphorane ylides from alkyl halides utilizing a new phenylsulfonyl reagent as the key reagent under mild reaction conditions in good overall yields.
2953 - 2958
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