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Dr Keith Andrews' Outputs (13)

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages. (2025)
Journal Article
Andrews, K. G. (2025). Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages. Beilstein Journal of Organic Chemistry, 21, 421-443. https://doi.org/10.3762/bjoc.21.30

The bespoke environments in enzyme active sites can selectively accelerate chemical reactions by as much as 1019. Macromolecular and supramolecular chemists have been inspired to understand and mimic these accelerations and selectivities for applicat... Read More about Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages..

Enzyme-like Acyl Transfer Catalysis in a Bifunctional Organic Cage (2024)
Journal Article
Andrews, K. G., Piskorz, T. K., Horton, P. N., & Coles, S. J. (2024). Enzyme-like Acyl Transfer Catalysis in a Bifunctional Organic Cage. Journal of the American Chemical Society, 146(26), 17887-17897. https://doi.org/10.1021/jacs.4c03560

Amide-based organic cage cavities are, in principle, ideal enzyme active site mimics. Yet, cage-promoted organocatalysis has remained elusive, in large part due to synthetic accessibility of robust and functional scaffolds. Herein, we report the acyl... Read More about Enzyme-like Acyl Transfer Catalysis in a Bifunctional Organic Cage.

Exploration of the polymorphic solid-state landscape of an amide-linked organic cage using computation and automation (2024)
Journal Article
Shields, C. E., Fellowes, T., Slater, A. G., Cooper, A., Andrews, K. G., & Szczypiński, F. T. (2024). Exploration of the polymorphic solid-state landscape of an amide-linked organic cage using computation and automation. Chemical Communications, 60(47), 6023-6026. https://doi.org/10.1039/d4cc01407c

Organic cages can possess complex, functionalised cavities that make them promising candidates for synthetic enzyme mimics. Conformationally flexible, chemically robust structures are needed for adaptable guest binding and catalysis, but rapidly exch... Read More about Exploration of the polymorphic solid-state landscape of an amide-linked organic cage using computation and automation.

Programmable synthesis of organic cages with reduced symmetry (2024)
Journal Article
Andrews, K. G., Horton, P. N., & Coles, S. J. (2024). Programmable synthesis of organic cages with reduced symmetry. Chemical Science, 15(17), 6536-6543. https://doi.org/10.1039/d4sc00889h

Integrating symmetry-reducing methods into self-assembly methodology is desirable to efficiently realise the full potential of molecular cages as hosts and catalysts. Although techniques have been explored for metal organic (coordination) cages, rati... Read More about Programmable synthesis of organic cages with reduced symmetry.

Silyl Esters as Reactive Intermediates in Organic Synthesis (2023)
Journal Article
Adler, M. J., D’Amaral, M. C., Andrews, K. G., & Denton, R. (2023). Silyl Esters as Reactive Intermediates in Organic Synthesis. Synthesis: Journal of Synthetic Organic Chemistry, 55(20), 3209-3238. https://doi.org/10.1055/a-2083-8591

Silyl esters have been exploited as metastable reaction intermediates, both purposefully and unintentionally, since at least the 1960s. Their reactivity is broadly related to the substituents on the silicon, and in this way their properties can be re... Read More about Silyl Esters as Reactive Intermediates in Organic Synthesis.

Redox-neutral organocatalytic Mitsunobu reactions (2019)
Journal Article
Beddoe, R. H., Andrews, K. G., Magné, V., Cuthbertson, J. D., Saska, J., Shannon-Little, A. L., …Denton, R. M. (2019). Redox-neutral organocatalytic Mitsunobu reactions. Science, 365(6456), 910-914. https://doi.org/10.1126/science.aax3353

The Mitsunobu reaction is widely used to invert the configuration of alcohols. However, its major drawback is the need to activate the alcohol with a full equivalent of phosphine, thereby generating a phosphine oxide co-product. Beddoe et al. report... Read More about Redox-neutral organocatalytic Mitsunobu reactions.

A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid (2017)
Journal Article
Andrews, K. G., Faizova, R., & Denton, R. M. (2017). A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid. Nature Communications, 8(1), https://doi.org/10.1038/ncomms15913

Amines are a fundamentally important class of biologically active compounds and the ability to manipulate their physicochemical properties through the introduction of fluorine is of paramount importance in medicinal chemistry. Current synthesis metho... Read More about A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid.

Improving the Accuracy of Computed 13C NMR Shift Predictions by Specific Environment Error Correction: Fragment Referencing (2013)
Journal Article
Andrews, K. G., & Spivey, A. C. (2013). Improving the Accuracy of Computed 13C NMR Shift Predictions by Specific Environment Error Correction: Fragment Referencing. Journal of Organic Chemistry, 78(22), 11302-11317. https://doi.org/10.1021/jo401833b

The accuracy of both Gauge-including atomic orbital (GIAO) and continuous set of gauge transformations (CSGT) 13C NMR spectra prediction by Density Functional Theory (DFT) at the B3LYP/6-31G** level is shown to be usefully enhanced by employing a ‘fr... Read More about Improving the Accuracy of Computed 13C NMR Shift Predictions by Specific Environment Error Correction: Fragment Referencing.

Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formedviaalkene metathesis from either a triene or a tetraene precursor (2013)
Journal Article
Andrews, K. G., Frampton, C. S., & Spivey, A. C. (2013). Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formedviaalkene metathesis from either a triene or a tetraene precursor. Acta crystallographica. Section C, Crystal structure communications, 69(11), 1207-1211. https://doi.org/10.1107/s010827011302492x

The identity of the major product of Ru-catalysed alkene metathesis of two polyene substrates has been determined using density functional theory (DFT) NMR prediction, a 1H–1H Total Correlated Spectroscopy (TOCSY) NMR experiment and ultimately by sin... Read More about Structural assignment of a bis-cyclopentenyl-β-cyanohydrin formedviaalkene metathesis from either a triene or a tetraene precursor.