An Efficient and Scalable One-Pot Double Michael Addition-Dieckmann Condensation for the Synthesis of 4,4-Disubstituted Cyclohexane β-Keto Esters

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Abstract

A simple, scalable, and efficient one-pot methodology for the synthesis of 4,4-disubstituted cyclohexane β-keto esters from benzylic nitriles or esters and methyl acrylate promoted by potassium tert-butoxide is described. The process relies on a tandem double Michael addition-Dieckmann condensation reaction, which results in the formation of three discrete carbon−carbon bonds in a single pot, including a quaternary center. The method allows for the convenient and rapid synthesis of a variety of 4-aryl-4-cyano-2-carbomethoxycyclohexanone and 4-aryl-2,4-biscarbomethoxycyclohexanone building blocks for use in natural products synthesis and medicinal chemistry.

Citing Articles

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

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  Chemistry of 2-Nitroglycals: A One-Pot Three-Component Stereoselective Approach toward 2-C-Branched O-Galactosides

  Pavan K. Kancharla and Yashwant D. Vankar
  The Journal of Organic Chemistry2010 75 (24), 8457-8464

  • Chemistry of 2-Nitroglycals: A One-Pot Three-Component Stereoselective Approach toward 2-C-Branched O-Galactosides

    Pavan K. Kancharla and Yashwant D. Vankar
    The Journal of Organic Chemistry2010 75 (24), 8457-8464

    A convenient one-pot three-component approach for the synthesis of 2-C-branched O-glycosides has been developed from 2-nitroglycals. These 2-C-branched sugars have been shown to be precursors for a variety of biologically and synthetically relevant ...

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

  Direct Synthesis of Highly Substituted 2-Cyclohexenones and Sterically Hindered Benzophenones Based on a [5C + 1C] Annulation

  Zhenqian Fu, Mang Wang, Ying Dong, Jun Liu and Qun Liu
  The Journal of Organic Chemistry2009 74 (16), 6105-6110

  • Direct Synthesis of Highly Substituted 2-Cyclohexenones and Sterically Hindered Benzophenones Based on a [5C + 1C] Annulation

    Zhenqian Fu, Mang Wang, Ying Dong, Jun Liu and Qun Liu
    The Journal of Organic Chemistry2009 74 (16), 6105-6110

    The regiospecific [5C + 1C] annulation of readily available α-alkenoyl ketene (S,S)-acetals 1 with aryl methyl ketones 2, the less active methylene compounds, has been developed. Upon treatment of 1 with 2 in the presence of t-BuOK in DMF at room ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  α-Alkenoyl Ketene S,S-Acetal-Based Multicomponent Reaction: An Efficient Approach for the Selective Construction of Polyfunctionalized Cyclohexanones

  Yuhui Ma, Mang Wang, Dan Li, Bahargul Bekturhun, Jun Liu and Qun Liu
  The Journal of Organic Chemistry2009 74 (8), 3116-3121

  • α-Alkenoyl Ketene S,S-Acetal-Based Multicomponent Reaction: An Efficient Approach for the Selective Construction of Polyfunctionalized Cyclohexanones

    Yuhui Ma, Mang Wang, Dan Li, Bahargul Bekturhun, Jun Liu and Qun Liu
    The Journal of Organic Chemistry2009 74 (8), 3116-3121

    A versatile multicomponent reaction based on the new four-carbon synthons α-alkenoyl ketene S,S-acetals 1 has been developed. This three-component reaction of readily available α-alkenoyl ketene S,S-acetals 1 with aldehydes 2 and active methylene ...

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

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