- Catalytic Hydrocyanation of Activated Terminal Alkynes
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A universal, practical and scalable organocatalytic hydrocyanation manifold to provide β-substituted acrylonitriles bearing an electron-withdrawing functionality has been implemented. The catalytic manifold operates under the reactivity generation principle “a good nucleophile generates a strong base”, and it uses 1,4-diazabicyclo[2.2.2]octane (DABCO) as the catalyst, activated terminal alkynes as substrates and acetone cyanohydrin as the cyanide source. The acrylonitriles obtained as E,Z mixtures are straightforwardly resolved by simple flash chromatography delivering the pure isomers in preparative amounts.
- Tejedor, David,Delgado-Hernández, Samuel,Colella, Lucía,García-Tellado, Fernando
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supporting information
p. 15046 - 15049
(2019/11/22)
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- Three-Component Synthesis of Quinolines Based on Radical Cascade Visible-Light Photoredox Catalysis
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Synthesis of highly substituted quinolines has been developed based on three-component radical cascade based on visible-light photoredox catalysis. This tandem coupling reaction has been coordinated to proceed with high chemoselectivity based on the differential electronic properties of coupling partners. Subjection of electron-rich β-aminoacrylates with electron-deficient halides and alkenes to the optimized conditions leads to the formation of quinolines in good yields after in situ oxidation of tetrahydroquinolines. Detailed mechanistic studies which reveal an unexpected reaction pathway is described. (Figure presented.).
- Choi, Jun-Ho,Park, Cheol-Min
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supporting information
p. 3553 - 3562
(2018/09/22)
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- [4 + 2] Cycloaddition reactions catalyzed by a chiral oxazaborolidinium cation. Reaction rates and diastereo-, regio-, and enantioselectivity depend on whether both bonds are formed simultaneously
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chemical equation presented The reaction rates and products in enantioselective Diels-Alder reactions with a range of dienophiles correlate with the expected degree of concertedness of bond formation in the transition state.
- Mukherjee, Santanu,Corey
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supporting information; experimental part
p. 1024 - 1027
(2010/06/15)
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