An Efficient Synthesis of Enamides from Ketones

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Abstract

A new synthesis of enamides from ketones is disclosed that involves a phosphine-mediated reductive acylation of oximes. The resulting enamides are isolated in good yields (up to 89%) and excellent purity, permitting a subsequent hydrogenation to access enantiopure acetamides at catalyst loadings practical for large-scale applications.

Citing Articles

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This article has been cited by 8 ACS Journal articles (5 most recent appear below).

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  Synthesis of Enamides via CuI-Catalyzed Reductive Acylation of Ketoximes with NaHSO₃

  Zheng-Hui Guan, Zhi-Yuan Zhang, Zhi-Hui Ren, Yao-Yu Wang, and Xumu Zhang
  The Journal of Organic Chemistry2011 76 (1), 339-341

  • Synthesis of Enamides via CuI-Catalyzed Reductive Acylation of Ketoximes with NaHSO₃

    Zheng-Hui Guan, Zhi-Yuan Zhang, Zhi-Hui Ren, Yao-Yu Wang, and Xumu Zhang
    The Journal of Organic Chemistry2011 76 (1), 339-341

    CuI-catalyzed reductive acylation of ketoximes for preparation of enamides was reported. A broad scope of enamides was obtained in high yields with NaHSO3 used as the terminal reductant.

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• 

  Rhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes

  Pei Chui Too, Yi-Feng Wang, and Shunsuke Chiba
  Organic Letters2010 12 (24), 5688-5691

  • Rhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes

    Pei Chui Too, Yi-Feng Wang, and Shunsuke Chiba
    Organic Letters2010 12 (24), 5688-5691

    A synthetic method of isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl2]2−NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C−H ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Regioselective Synthesis of Heterocycles Containing Nitrogen Neighboring an Aromatic Ring by Reductive Ring Expansion Using Diisobutylaluminum Hydride and Studies on the Reaction Mechanism

  Hidetsura Cho, Yusuke Iwama, Kenji Sugimoto, Seiji Mori and Hidetoshi Tokuyama
  The Journal of Organic Chemistry2010 75 (3), 627-636

  • Regioselective Synthesis of Heterocycles Containing Nitrogen Neighboring an Aromatic Ring by Reductive Ring Expansion Using Diisobutylaluminum Hydride and Studies on the Reaction Mechanism

    Hidetsura Cho, Yusuke Iwama, Kenji Sugimoto, Seiji Mori and Hidetoshi Tokuyama
    The Journal of Organic Chemistry2010 75 (3), 627-636

    A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic rings with diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  A Facile and Practical Synthesis of N-Acetyl Enamides

  Wenjun Tang, Andrew Capacci, Max Sarvestani, Xudong Wei, Nathan K. Yee and Chris H. Senanayake
  The Journal of Organic Chemistry2009 74 (24), 9528-9530

  • A Facile and Practical Synthesis of N-Acetyl Enamides

    Wenjun Tang, Andrew Capacci, Max Sarvestani, Xudong Wei, Nathan K. Yee and Chris H. Senanayake
    The Journal of Organic Chemistry2009 74 (24), 9528-9530

    A facile and practical method for the synthesis of N-acetyl α-arylenamides has been developed from corresponding ketoximes as the starting materials with ferrous acetate as the reducing reagent. This methodology offers mild reaction conditions, simple ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  New Efficient Asymmetric Synthesis of Taranabant, a CB1R Inverse Agonist for the Treatment of Obesity

  Debra J. Wallace, Kevin R. Campos, C. Scott Shultz, Artis Klapars, Daniel Zewge, Brian R. Crump, Brian D. Phenix, J. Christopher McWilliams, Shane Krska, Yongkui Sun, Cheng-yi Chen and Felix Spindler
  Organic Process Research & Development2009 13 (1), 84-90

  • New Efficient Asymmetric Synthesis of Taranabant, a CB1R Inverse Agonist for the Treatment of Obesity

    Debra J. Wallace, Kevin R. Campos, C. Scott Shultz, Artis Klapars, Daniel Zewge, Brian R. Crump, Brian D. Phenix, J. Christopher McWilliams, Shane Krska, Yongkui Sun, Cheng-yi Chen and Felix Spindler
    Organic Process Research & Development2009 13 (1), 84-90

    Taranabant (1) is a cannabinoid-1 receptor (CB1R) inverse agonist that was recently in late-stage clinical development for the treatment of obesity. The previously employed synthesis exhibited a number of shortcomings for continuing development, and in ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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