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The Gaunt Group

@gauntgroup.bsky.social

Synthesis. Catalysis. Biology. Technology. Research group @cambridge-uni.bsky.social. Student-run account. Formal enquiries should be directed to MJG.

89 Followers  |  1 Following  |  8 Posts  |  Joined: 12.11.2024  |  1.5122

Latest posts by gauntgroup.bsky.social on Bluesky

One-carbon homologation of alkenes - Nature Nature - One-carbon homologation of alkenes

Congrats to Marcus on this years-long effort. Read it at doi.org/10.1038/s41586-025-09159-9

#ChemSky βš—οΈπŸ§ͺ (3/3)

22.05.2025 10:08 β€” πŸ‘ 0    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0
Scheme showing a chemical reaction from Cyclosporin A to homo-Cyclosporin A. The novel one carbon homologation acts on the internal alkene in the WHO essential medicine Cyclosporin A and homologates it to give a novel analog with unexplore properties.

Scheme showing a chemical reaction from Cyclosporin A to homo-Cyclosporin A. The novel one carbon homologation acts on the internal alkene in the WHO essential medicine Cyclosporin A and homologates it to give a novel analog with unexplore properties.

Our methodology demonstrates broad applicability across a diverse range of highly functionalised alkene substrates. It homologates terminal and internal alkenes and complex molecules like Cyclosporine A, enabling the synthesis of analogs with modified ​biological properties. (2/3)

22.05.2025 10:08 β€” πŸ‘ 3    πŸ” 0    πŸ’¬ 1    πŸ“Œ 0
Scheme showcasing and explaining the novel one-carbon alkene homologation. An (allyl)siloxymethylsulfone reagent is attached to the alkene via cross metathesis, deprotected via acid-mediated fragmentation to the sulfinic acid, and undergoes the retro-ene to deliver the homologated alkene. This reaction works across a broad scope of simple and complex alkenes, including monosubstituted, 1,1-disubstituted and 1,2-disubstituted internal alkenes.

Scheme showcasing and explaining the novel one-carbon alkene homologation. An (allyl)siloxymethylsulfone reagent is attached to the alkene via cross metathesis, deprotected via acid-mediated fragmentation to the sulfinic acid, and undergoes the retro-ene to deliver the homologated alkene. This reaction works across a broad scope of simple and complex alkenes, including monosubstituted, 1,1-disubstituted and 1,2-disubstituted internal alkenes.

Excited to share that our one-carbon alkene homologation has been published in @nature.com. πŸŽ‰ Marcus developed a simple reagent that enables the homologation of alkenes by a one-pot cross metathesis-fragmentation-retro-ene cascade giving easy access to the homologated alkene. (1/3) 🧡

22.05.2025 10:08 β€” πŸ‘ 5    πŸ” 1    πŸ’¬ 1    πŸ“Œ 0
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Some Items of Interest to Process R&D Chemists and Engineers

Happy to see our Carbonyl Azinylative Amination highlighted in @acs.org OPR&Ds new items of interest. Alex, Roopender and Rachel's work uses in situ generated heteroarylindium species to form diverse heteroarylaklyamines from three readily available starting materials.

pubs.acs.org/doi/10.1021/...

22.01.2025 09:50 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0
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Pd-Catalyzed C–H Activation vs Ξ²-H Elimination: An Experimental and Computational Insight into the Reactivity of Tertiary Alkylamines Tertiary alkylamines can coordinate palladium salts and direct C–H activation reactions. However, these tertiary alkylamines can suffer from decomposition through oxidative pathways. This report descr...

Find this work at pubs.acs.org/doi/10.1021/...

16.12.2024 23:38 β€” πŸ‘ 2    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0
A graphic showing a central chemical structure of a palladium-coordinated central N-alkyl piperidine which then undergoes either productive Ξ³-C-H cleavage or decomposition via Ξ²-H elimination. DFT structures highlight how an N-Ac amino acid ligand favours the productive Ξ³-C-H cleavage due to geometic restriction around the Pd-centre.

Find this work at https://pubs.acs.org/doi/10.1021/acscatal.4c06160

A graphic showing a central chemical structure of a palladium-coordinated central N-alkyl piperidine which then undergoes either productive Ξ³-C-H cleavage or decomposition via Ξ²-H elimination. DFT structures highlight how an N-Ac amino acid ligand favours the productive Ξ³-C-H cleavage due to geometic restriction around the Pd-centre. Find this work at https://pubs.acs.org/doi/10.1021/acscatal.4c06160

Check out our new work in 3Β° alkylamine directed #Pd catalysed C-H activation in #ACSCatalysis. Jesus shows how an amino acid ligand favours one CMD pathways to preferentially give Ξ³-C(sp3)-H actiavtion over Ξ²-H elimination enabling us to make some strained 4Β° centres.

#ChemSky πŸ§ͺβš—οΈ

16.12.2024 23:38 β€” πŸ‘ 4    πŸ” 1    πŸ’¬ 1    πŸ“Œ 0
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Some Items of Interest to Process R&D Chemists and Engineers OR SEARCH CITATIONS

We are thrilled to see our recent work on carbonyl acylative amination be highlighted in #OPRD. Congrats once more to our colleague Dr. Jianzhong Liu, who is starting his own lab at the University of Science and Technology of China (USTC).

#ChemSky βš—οΈπŸ§ͺ

pubs.acs.org/doi/10.1021/...

11.12.2024 15:38 β€” πŸ‘ 4    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0
A celebration in the Gaunt Group's lab kitchen including Matthew Gaunt and the newly graduated Dr. Joe Phelps.

A celebration in the Gaunt Group's lab kitchen including Matthew Gaunt and the newly graduated Dr. Joe Phelps.

Congratulations on Dr. Joe Phelps for passing his viva πŸŽ‰πŸŽ‰!!
#ChemSky πŸ§ͺβš—οΈ

26.11.2024 10:37 β€” πŸ‘ 4    πŸ” 0    πŸ’¬ 0    πŸ“Œ 0

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