All Outputs (11)

Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans (2024)
Journal Article
Arnold, R. E., Saska, J., Mesquita-Ribeiro, R., Dajas-Bailador, F., Taylor, L., Lewis, W., Argent, S., Shao, H., Houk, K. N., & Denton, R. M. (2024). Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans. Chemical Science, 15(30), 11783-11793. https://doi.org/10.1039/d4sc03232b

We report the first total syntheses of simonsol F (3), simonsinol (5), fargenin (4), and macranthol (6) in addition to syntheses of simonsol C (2), simonsol G (1), and honokiol (14). The syntheses are based upon a phosphonium ylide-mediated cascade r... Read More about Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans.

Synthesis, structure and stereodynamics of atropisomeric N-chloroamides (2024)
Journal Article
Campbell, A. D. G., Roper, N. J., Waddell, P. G., Wills, C., Dixon, C. M., Denton, R. M., …Armstrong, R. J. (2024). Synthesis, structure and stereodynamics of atropisomeric N-chloroamides. Chemical Communications, 60(28), 3818-3821. https://doi.org/10.1039/d4cc00268g

Atropisomeric N-chloroamides were efficiently accessed by electrophilic halogenation of ortho-substituted secondary anilides. The stereodynamics of atropisomerism in these novel scaffolds was interrogated by detailed experimental and computational st... Read More about Synthesis, structure and stereodynamics of atropisomeric N-chloroamides.

Silyl Esters as Reactive Intermediates in Organic Synthesis (2023)
Journal Article
D'Amaral, M. C., Andrews, K. G., Denton, R., & Adler, M. J. (2023). Silyl Esters as Reactive Intermediates in Organic Synthesis. SYNTHESIS, 20(55), 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.

Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SN2-Displacement of Kukhtin–Ramirez Intermediates (2022)
Journal Article
Calcatelli, A., Denton, R. M., & Ball, L. T. (2022). Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SN2-Displacement of Kukhtin–Ramirez Intermediates. Organic Letters, https://doi.org/10.1021/acs.orglett.2c03201

We report a concise and modular approach to α,α-diaryl α-amino esters from readily available α-keto esters. This mild, one-pot protocol proceeds via ketone umpolung, with in situ formation of a Kukhtin-Ramirez intermediate preceding sequential electr... Read More about Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SN2-Displacement of Kukhtin–Ramirez Intermediates.

In situ silane activation enables catalytic reduction of carboxylic acids (2022)
Journal Article
Stoll, E. L., Barber, T., Hirst, D. J., & Denton, R. M. (2022). In situ silane activation enables catalytic reduction of carboxylic acids. Chemical Communications, 58(21), 3509-3512. https://doi.org/10.1039/D1CC03396D

We describe a catalytic system for the conversion of carboxylic acids into alcohols using substoichiometric zinc acetate and N-methyl morpholine, in combination with phenylsilane as the nominal terminal reductant. Reaction monitoring by 19F NMR spect... Read More about In situ silane activation enables catalytic reduction of carboxylic acids.

A Practical Catalytic Reductive Amination of Carboxylic Acids (2020)
Journal Article
Stoll, E., Tongue, T., Andrews, K. G., Valette, D., Hirst, D. J., & Denton, R. M. (2020). A Practical Catalytic Reductive Amination of Carboxylic Acids. Chemical Science, 11(35), 9494-9500. https://doi.org/10.1039/d0sc02271c

We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide red... Read More about A Practical Catalytic Reductive Amination of Carboxylic Acids.

Synthesis of 18O-labelled alcohols from unlabelled alcohols (2020)
Journal Article
Beddoe, R. H., Edwards, D. C., Goodman, L., Sneddon, H. F., & Denton, R. M. (2020). Synthesis of 18O-labelled alcohols from unlabelled alcohols. Chemical Communications, 56(48), 6480-6483. https://doi.org/10.1039/d0cc02855j

The synthesis of primary, secondary and tertiary 18O-enriched alcohols from readily available 16O-alcohols via a Mitsunobu esterification and hydrolysis is described. The method is further exemplified in the labelling of the active pharmaceutical ing... Read More about Synthesis of 18O-labelled alcohols from unlabelled alcohols.

The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art (2018)
Journal Article
Beddoe, R. H., Sneddon, H. F., & Denton, R. M. (2018). The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art. Organic and Biomolecular Chemistry, 42(16), 7774-7781. https://doi.org/10.1039/c8ob01929k

The Mitsunobu reaction is widely regarded as the pre-eminent method for performing nucleophilic substitutions of alcohols with inversion of configuration. However, its applicability to large-scale synthesis is undermined by the fact that alcohol acti... Read More about The catalytic Mitsunobu reaction: a critical analysis of the current state-of-the-art.

Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions (2016)
Journal Article
Saska, J., Lewis, W., Paton, R., & Denton, R. (2016). Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions. Chemical Science, 7(12), 7040-7049. https://doi.org/10.1039/C6SC03012B

We report a 12-step catalytic enantioselective formal synthesis of malhamensilipin A (3) and diastereoisomeric analogues from (E)-2-undecenal. The convergent synthesis relied upon iterative epoxidation and phosphorus(V)-mediated deoxydichlorination r... Read More about Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions.

Synthesis of quaternary aryl phosphonium salts: photoredox-mediated phosphine arylation (2016)
Journal Article
Fearnley, A., An, J., Jackson, M., Lindovska, P., & Denton, R. (2016). Synthesis of quaternary aryl phosphonium salts: photoredox-mediated phosphine arylation. Chemical Communications, 52, https://doi.org/10.1039/C6CC00556J

We report a synthesis method for the construction of quaternary aryl phoshonium salts at ambient temperature. The regiospecific reaction invovles the coupling of phosphines with aryl radicals derived from diaryliodonium salts under photoredox conditi... Read More about Synthesis of quaternary aryl phosphonium salts: photoredox-mediated phosphine arylation.

Development of a redox-free mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes (2014)
Journal Article
Tang, X., Chapman, C., Whiting, M., & Denton, R. M. (in press). Development of a redox-free mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes. Chemical Communications, 50, https://doi.org/10.1039/C4CC02171A

The development of the first redox-free protocol for the Mitsunobu reaction is described. This has been achieved by exploiting triphenylphosphine oxide – the unwanted by-product in the conventional Mitsunobu reaction – as the precursor to the active... Read More about Development of a redox-free mitsunobu reaction exploiting phosphine oxides as precursors to dioxyphosphoranes.