gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones
PhSCF2SiMe3has been demonstrated as difluoromethyl carbanion synthon (-CF2H). It reacts chemoselectively with α- and γ-ketoesters at the keto group in the presence of a catalytic amount of TBAF in THF to give the corresponding α-hydroxy ester adducts as well as γ-gem-difluorophenylsulfanylmethylated...
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| Main Authors: | , , , |
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| 格式: | Article |
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2018
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| 在線閱讀: | https://repository.li.mahidol.ac.th/handle/123456789/24118 |
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| 總結: | PhSCF2SiMe3has been demonstrated as difluoromethyl carbanion synthon (-CF2H). It reacts chemoselectively with α- and γ-ketoesters at the keto group in the presence of a catalytic amount of TBAF in THF to give the corresponding α-hydroxy ester adducts as well as γ-gem-difluorophenylsulfanylmethylated-γ-butyrolactones in good yields. Reductive cleavage of the phenylsulfanyl group of these products employing Bu3SnH/AIBN gives the corresponding gem-difluoromethylated α-hydroxyesters and γ-butyrolactones in good yields. © 2007 Elsevier Ltd. All rights reserved. |
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