Pyrroline

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Tetsuro Shinada - One of the best experts on this subject based on the ideXlab platform.

  • Short Total Synthesis of (−)-Kainic Acid
    Organic letters, 2014
    Co-Authors: Yasufumi Ohfune, Tetsuro Shinada
    Abstract:

    A short total synthesis of (−)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition–cyclization reaction, which provided access to a chiral Pyrroline in a highly stereoselective manner. The chiral Pyrroline was converted to (−)-kainic acid via the stereoselective 1,4-reduction of the Pyrroline double bond in three steps.

  • short total synthesis of kainic acid
    Organic Letters, 2014
    Co-Authors: Yasufumi Ohfune, Tetsuro Shinada
    Abstract:

    A short total synthesis of (−)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition–cyclization reaction, which provided access to a chiral Pyrroline in a highly stereoselective manner. The chiral Pyrroline was converted to (−)-kainic acid via the stereoselective 1,4-reduction of the Pyrroline double bond in three steps.

Yasufumi Ohfune - One of the best experts on this subject based on the ideXlab platform.

  • Short Total Synthesis of (−)-Kainic Acid
    Organic letters, 2014
    Co-Authors: Yasufumi Ohfune, Tetsuro Shinada
    Abstract:

    A short total synthesis of (−)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition–cyclization reaction, which provided access to a chiral Pyrroline in a highly stereoselective manner. The chiral Pyrroline was converted to (−)-kainic acid via the stereoselective 1,4-reduction of the Pyrroline double bond in three steps.

  • short total synthesis of kainic acid
    Organic Letters, 2014
    Co-Authors: Yasufumi Ohfune, Tetsuro Shinada
    Abstract:

    A short total synthesis of (−)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition–cyclization reaction, which provided access to a chiral Pyrroline in a highly stereoselective manner. The chiral Pyrroline was converted to (−)-kainic acid via the stereoselective 1,4-reduction of the Pyrroline double bond in three steps.

Teck-peng Loh - One of the best experts on this subject based on the ideXlab platform.

  • visible light promoted carboimination of unactivated alkenes for the synthesis of densely functionalized Pyrroline derivatives
    ACS Catalysis, 2016
    Co-Authors: Sai-hu Cai, Jia-hao Xie, Shengjin Song, Chao Feng, Teck-peng Loh
    Abstract:

    An efficient strategy which integrates visible-light-induced iminyl-radical formation with carboimination of unactivated alkenes has been developed for the easy access of densely functionalized Pyrroline derivatives. With fac-[Ir(ppy)3] as photoredox catalyst, the acyl oximes were converted into iminyl radical intermediates by one electron reduction, and evolve through a cascade of intramolecular cyclization and intermolecular carbon radical trapping to give the functionalized Pyrrolines. The utilization of silyl enol ethers as coupling partners not only allows the introduction of synthetically useful ketone functionalities but also renders catalyst regeneration without any external reductants. This protocol is characterized by its mild reaction conditions and the tolerance of a broad range of functionalities.

  • Visible-Light-Promoted Carboimination of Unactivated Alkenes for the Synthesis of Densely Functionalized Pyrroline Derivatives
    2016
    Co-Authors: Sai-hu Cai, Jia-hao Xie, Shengjin Song, Chao Feng, Teck-peng Loh
    Abstract:

    An efficient strategy which integrates visible-light-induced iminyl-radical formation with carboimination of unactivated alkenes has been developed for the easy access of densely functionalized Pyrroline derivatives. With fac-[Ir­(ppy)3] as photoredox catalyst, the acyl oximes were converted into iminyl radical intermediates by one electron reduction, and evolve through a cascade of intramolecular cyclization and intermolecular carbon radical trapping to give the functionalized Pyrrolines. The utilization of silyl enol ethers as coupling partners not only allows the introduction of synthetically useful ketone functionalities but also renders catalyst regeneration without any external reductants. This protocol is characterized by its mild reaction conditions and the tolerance of a broad range of functionalities

Jetze J. Tepe - One of the best experts on this subject based on the ideXlab platform.

Bruce E. Maryanoff - One of the best experts on this subject based on the ideXlab platform.