Stabilized Nucleophiles with Electron Deficient Alkenes and Alkynes

Jung, Michael E.

doi:10.1016/b978-0-08-052349-1.00090-1

Cited by 162 publications

(28 citation statements)

References 606 publications

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“…5,8,10,22 To ensure orthogonal labeling of the proposed bis-enone product over the starting BCH functionality, we explored the use of conjugate addition by secondary amines (Scheme 2). 23 When small molecule analogue 5 22 was exposed to 9-methylaminomethyl anthracene (MAMA) (5 equiv, 0.25 M) in MeCN overnight, no change was observed in the 1 H NMR spectrum. Alternatively, when a bis-enone analogue 4 was subjected to identical conditions, the primary product observed was the mono-MAMA adduct (see Supporting Information).…”

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confidence: 99%

Bicyclo[3.2.0]heptane Mechanophores for the Non-scissile and Photochemically Reversible Generation of Reactive Bis-enones

et al. 2012

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Force induced transformations of polymer bound functionalities have the potential to produce a rich array of stress responsive behavior. One area of particular interest is the activation of non-scissile mechanophores in which latent reactivity can be unveiled that, under the appropriate conditions, could lead to constructive bond formation in materials exposed to typically destructive stress. Here, the mechanical activation of a bicyclo[3.2.0]heptane (BCH) mechanophore is demonstrated via selective labeling of bis-enone products. BCH ring-opening produces large local elongation (> 4 Å) and products that are reactive to conjugate additions under mild conditions. Subsequent photocyclization regenerates the initial BCH functionality, providing switchable structure and reactivity along the polymer backbone in response to stress and visible light.

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confidence: 99%

Bicyclo[3.2.0]heptane Mechanophores for the Non-scissile and Photochemically Reversible Generation of Reactive Bis-enones

et al. 2012

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“…Two possible mechanisms can be proposed for the reaction of 1b with 8a to form diastereoisomers 29b and 30b (Figure ). The first is a two‐step pathway, including the formation of zwitterionic intermediate I from the 1,4‐conjugated addition of 1b to 8a (path a) . The second one may occur through a concerted hetero‐Diels‐Alder cycloaddition (path b) …”

Section: Resultsmentioning

confidence: 99%

Enantiopure 4‐oxazolin‐2‐ones and 4‐methylene‐2‐oxazolidinones as chiral building blocks in a divergent asymmetric synthesis of heterocycles

et al. 2019

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Enantiopure 3‐((R)‐ and 3‐((S)‐1‐phenylethyl)‐4‐oxazoline‐2‐ones were evaluated as chiral building blocks for the divergent construction of heterocycles with stereogenic quaternary centers. The N‐(R)‐ or N‐(S)‐1‐phenylethyl group of these compounds proved to be an efficient chiral auxiliary for the asymmetric induction of the 4‐ and 5‐positions of the 4‐oxazolin‐2‐one ring through thermal and MW‐promoted nucleophilic conjugated addition to Michael acceptors and alkyl halides. The resulting adducts were transformed via a cascade process into fused six‐membered carbo‐ and heterocycles. The structure of the reaction products depended on the electrophiles and reaction conditions used. Alternative isomeric 4‐methylene‐2‐oxazolidinones served as chiral precursors for a versatile and divergent approach to highly substituted cyclic carbamates. DFT quantum calculations showed that the formation of bicyclic pyranyl compounds was generated by a diastereoselective concerted hetero‐Diels‐Alder cycloaddition.

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“…[20] The two different types of ionic liquid-functionalized SBA-15 (ILSBA-1 Owing to their prevalence and wide utility in organic synthesis, the development of novel synthetic methods leading to β-amino ketones or their derivatives has attracted much attention in recent years. [21] Recently, there were also some reports of azaMichael reaction conducted in Cu(acac) 2 [23]. Unfortunately, many of these procedures often require an excess of reagents, long reaction times, use of expensive heavy metal salts and drastic reaction conditions in CH 3 CN or CH 2 Cl 2 that are toxic organic solvents.…”

Section: Resultsmentioning

confidence: 99%

Ionic liquid-functionalized SBA-15 mesoporous material: efficient heterogeneous catalyst in versatile organic reactions

Yang

Jiang

et al. 2007

Open Chemistry

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Ionic liquid-functionalized mesoporous materials exhibited high catalytic activity in versatile organic reactions, such as cycloaddition of carbon dioxide (CO 2 ) with epoxide, aza-Michael addition of amines to α, β-unsaturated carbonyl compounds, and the Biginelli reaction of aldehyde, ethyl acetoacetate and urea. Recycling of the catalyst in these reactions could be carried out and the catalyst used at least five times without significant loss in activity.

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Stabilized Nucleophiles with Electron Deficient Alkenes and Alkynes

Cited by 162 publications

References 606 publications

Bicyclo[3.2.0]heptane Mechanophores for the Non-scissile and Photochemically Reversible Generation of Reactive Bis-enones

Bicyclo[3.2.0]heptane Mechanophores for the Non-scissile and Photochemically Reversible Generation of Reactive Bis-enones

Enantiopure 4‐oxazolin‐2‐ones and 4‐methylene‐2‐oxazolidinones as chiral building blocks in a divergent asymmetric synthesis of heterocycles

Ionic liquid-functionalized SBA-15 mesoporous material: efficient heterogeneous catalyst in versatile organic reactions

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