Asymmetric conjugate addition–cyclization of cyclohexane-1,2-dione with alkylidenemalononitriles using diaminomethylenemalononitrile organocatalyst

Matsushima, Yasuyuki; Iino, Yuta; Tsuruta, Yuka; Nakashima, Kosuke; Hirashima, Shin‐ichi; Miura, Tsuyoshi

doi:10.1016/j.tetlet.2022.153773

Cited by 6 publications

(1 citation statement)

References 36 publications

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“…Based on the stereochemistry of the obtained adducts 3 , we guess that the reaction proceeds via a similar transition state in our previous report [7f] (Figure 2). The quinuclidine group's tertiary amine in C9 initially abstracts a proton from β‐keto esters 1 , forming a reactive enolate.…”

Section: Resultssupporting

confidence: 78%

Organocatalyzed Synthesis of Bicyclic γ‐Lactam Derivatives via Asymmetric Conjugate Addition of Cyclic β‐Keto Esters to Benzoyl Acrylonitriles

Matsushima,

Kubokawa,

Watanabe

et al. 2023

Asian J Org Chem

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A diaminomethylenemalononitrile organocatalyst efficiently promoted the asymmetric conjugate addition of cyclic β‐keto esters to benzoyl acrylonitriles to afford the corresponding adducts. This was followed by the transformation of the nitrile group into an amide group, resulting in bicyclic γ‐lactam derivatives in good yields with excellent enantioselectivities (up to 99 % ee). As far as we know, this is the first study to synthesize chiral bicyclic γ‐lactam derivatives from cyclic β‐keto esters and benzoyl acrylonitriles.

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Section: Resultssupporting

confidence: 78%

Organocatalyzed Synthesis of Bicyclic γ‐Lactam Derivatives via Asymmetric Conjugate Addition of Cyclic β‐Keto Esters to Benzoyl Acrylonitriles

Matsushima,

Kubokawa,

Watanabe

et al. 2023

Asian J Org Chem

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Asymmetric Direct Vinylogous Conjugate Addition of α,β‐Unsaturated γ‐Butyrolactam to Acyl Acrylonitriles using Organocatalysts

et al. 2023

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Thiourea organocatalyst efficiently promotes the asymmetric direct vinylogous conjugate addition of α,β‐unsaturated γ‐butyrolactam to benzoyl acrylonitriles, resulting in corresponding addition products with good yields and excellent stereoselectivities (up to 99% ee). This report is the first study demonstrating the asymmetric direct vinylogous conjugate addition of α,β‐unsaturated γ‐butyrolactam to benzoyl acrylonitriles.

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Catalytic Synthesis of Phthalide Derivatives via Asymmetric Bromolactonization of Stilbene‐type Carboxylic Acids usingN,N‐Dibenzyl Diaminomethylenemalononitrile as Organocatalyst

et al. 2023

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The asymmetric 5‐exo bromolactonization of stilbene‐type carboxylic acids could be achieved using a N,N‐dibenzyl diaminomethylenemalononitrile organocatalyst with high yields and excellent enantioselectivities (up to 92% ee) of the corresponding phthalide derivatives. This is the first report where the successful synthesis of the phthalide derivatives as the main product, with high optical purity, could be achieved using the asymmetric 5‐exo bromolactonization of the stilbene‐type carboxylic acids with various substituents.

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Asymmetric conjugate addition–cyclization of cyclohexane-1,2-dione with alkylidenemalononitriles using diaminomethylenemalononitrile organocatalyst

Cited by 6 publications

References 36 publications

Organocatalyzed Synthesis of Bicyclic γ‐Lactam Derivatives via Asymmetric Conjugate Addition of Cyclic β‐Keto Esters to Benzoyl Acrylonitriles

Organocatalyzed Synthesis of Bicyclic γ‐Lactam Derivatives via Asymmetric Conjugate Addition of Cyclic β‐Keto Esters to Benzoyl Acrylonitriles

Asymmetric Direct Vinylogous Conjugate Addition of α,β‐Unsaturated γ‐Butyrolactam to Acyl Acrylonitriles using Organocatalysts

Catalytic Synthesis of Phthalide Derivatives via Asymmetric Bromolactonization of Stilbene‐type Carboxylic Acids usingN,N‐Dibenzyl Diaminomethylenemalononitrile as Organocatalyst

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