Synthesis of carbazoloquinone natural products ‘on-water’

Norcott, Philip; McErlean, Christopher S. P.

doi:10.1039/c5ob00852b

Cited by 11 publications

(6 citation statements)

References 30 publications

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“…76 A further in-water/on-water domino process was explored in 2015 where the McErlean and Norcott examined the synthesis of königinequinone A which offered a route to other natural products murrayquinone B, C, D and E though an on-water Claisen rearrangement. 77 The scope of reactions which have been explored using onwater conditions continues to grow and water can offer advantages over organic solvents. However, this is reaction specific and in many cases this is still an emerging area of research where in-depth mechanistic studies are needed in order to deduce the role water plays in these reactions.…”

Section: Organocatalysismentioning

confidence: 99%

Organic synthesis reactions on-water at the organic–liquid water interface

2016

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Organic reactions that occur at the water interface for water-insoluble compounds, and reactions in water solution for water soluble compounds, has added a powerful dimension to prospects for organic synthesis under more beneficial economic and environmental conditions. Many organic molecules are partially soluble in water and reactions that appear as heterogeneous mixtures and suspensions may involve on-water and in-water reaction modes occurring simultaneously. The behavior of water molecules and organic molecules at this interface is discussed in the light of reported theoretical and experimental studies. The on-water catalytic effect, relative to neat reactions or organic solvents, ranges from factors of several hundred times to 1-2 times and it depends on the properties of reactant compounds. In some cases when on-water reactions produce quantitative yields of water-insoluble products they can reach ideal synthetic aspirations.

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Section: Organocatalysismentioning

confidence: 99%

Organic synthesis reactions on-water at the organic–liquid water interface

2016

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“…General remarks: 3-Aminophenyl acetate 7, [39] tris(p-tertbutylphenyl)methanol 8, [30] amino phenol stopper 9, [31] macrocycle precursor 14 [13] and [2]rotaxane 1 • PF 6 [13] were prepared as previously described. Other compounds were bought from commercial suppliers and used as received.…”

Section: Methodsmentioning

confidence: 99%

Hydroxy Groups Enhance [2]Rotaxane Anion Binding Selectivity

Goodwin

Docker

MacDermott-Opeskin

et al. 2022

Chemistry A European J

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We report the synthesis of two [2]rotaxanes containing an interlocked three dimensional binding cavity formed from a pyridinium bis(amide) axle component containing two phenol donors, and an isophthalamide based macrocycle. In the competitive solvent mixture 1 : 1 CDCl 3 : CD 3 OD, one of the receptors exhibits a much higher selectivity preference for chloride than an analogous rotaxane without the hydroxy groups. X-ray crystal structures reveal the chloride anion guest encapsulated within the interlocked binding cavity, though not all of the hydrogen bond donors are utilised. Computational semi-empirical simulations indicate that secondary intermolecular interactions occur between the axle hydroxy hydrogen bond donors and the [2]rotaxane macrocycle components, contributing to a more preorganised binding pocket, which may be responsible for the observed enhanced selectivity.

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“…General remarks: 3-Aminophenyl acetate 7, 38 tris(p-tertbutylphenyl)methanol 8, 30 amino phenol stopper 9, 31 macrocycle precursor 14 13 and [2]rotaxane 1•PF6 13 were prepared as previously described. Other compounds were bought from commercial suppliers and used as received.…”

Section: Methodsmentioning

confidence: 99%

Hydroxy groups enhance [2]rotaxane anion binding selectivity

Goodwin

Docker

MacDermott-Opeskin

et al. 2022

Preprint

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We report the synthesis of two [2]rotaxanes containing an interlocked three dimensional binding cavity formed from a pyridinium bis(amide) axle component containing two phenol donors, and an isophthalamide based macrocycle. In the competitive solvent mixture 1:1 CDCl3:CD3OD, one of the receptors exhibits a much higher selectivity preference for chloride than an analogous rotaxane without the hydroxy groups. X-ray crystal structures reveal the chloride anion guest encapsulated within the interlocked binding cavity, though not all of the hydrogen bond donors are utilised. Computational semiempirical simulations indicate that secondary intermolecular interactions occur between the axle hydroxy hydrogen bond donors and the [2]rotaxane macrocycle components, contributing to a more preorganised binding pocket, which may be responsible for the observed enhanced selectivity.

show abstract

Synthesis of carbazoloquinone natural products ‘on-water’

Cited by 11 publications

References 30 publications

Organic synthesis reactions on-water at the organic–liquid water interface

Organic synthesis reactions on-water at the organic–liquid water interface

Hydroxy Groups Enhance [2]Rotaxane Anion Binding Selectivity

Hydroxy groups enhance [2]rotaxane anion binding selectivity

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