Synthetic Organic Chemistry & Catalysis • University of Oxford

Martin Smith Research Group

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We are a synthetic chemistry research group with a focus on enantioselective catalysis, photocatalysis and the synthesis of complex molecules. We are based in the Chemistry Research Laboratory at the University of Oxford


Our work on building a configurationally stable chiral non-racemic molecule in which the oxygen atom is the sole stereogenic centre is featured as one of C&EN's molecules of the year 2023 (and makes it onto the cover).

Read the highlight in C&EN: C&EN's molecules of 2023

Control of stereogenic oxygen in a helically chiral oxonium ion
Nature DOI: 10.1038/s41586-023-05719-z

Our most recent paper in ChemRxiv reports on a collaboration with the Donohoe group that shows how protecting a key catalytic iridium hydride intermediate in hydrogen borrowing C-alkylation enables remarkable functional group tolerance. Lots of interesting heterocycles are viable substrates under these conditions. Great stuff from Elliot!

Functional Group Tolerant Hydrogen Borrowing C-Alkylation
ChemRxiv: DOI: 10.26434/chemrxiv-2023-30399

Our latest paper outlines how triaryl oxonium ions can be employed in an ultra-mild and functional group tolerant method to generate and trap arynes and hetarynes. This synthetic/computational collaboration with the Burton and Paton groups outlines how the oxonium ion is both a powerful electron-withdrawing group and a great leaving group.

Harnessing Oxonium Ions for Aryne Generation
Nature Synthesis: DOI: 10.1038/s44160-023-00408-1

Read the highlight in Nature Synthesis: Oxonium ions for Easy Aryne Chemistry

Our paper describing the synthesis and characterisation of a helically chiral triaryloxonium ion is now online. This collaborative study with the Burton and Paton groups describes a configurationally stable chiral non-racemic molecule in which the oxygen atom is the sole stereogenic centre. A great synthetic-computational collaboration - and wonderful work from Owen, Maddie and Mihai!

Control of stereogenic oxygen
in a helically chiral oxonium ion

Nature DOI: 10.1038/s41586-023-05719-z

Read the highlight in C&EN: This New Molecule Owes its Chirality to Oxygen Alone
Read the highlight in Chemistry World: New Example of Molecular Chirality Discovered
Read the highlight in Science Link: Helix 'Catches' Chiral Oxygen
Read the highlight in Synfacts: Chirality at Oxygen!
Read the highlight at Chemists synthesise and characterise novel helically chiral oxonium ion with a stereogenic oxygen atom

in ChemRxiv we report a visible light mediated reaction that combines diradical reactivity and zwitterion chemistry to intercept the classical Staudinger ketene-imine cyclisation en route to β-lactams. This collaboration with the Paton and Alegre groups explores the mechanistic conundrum behind this fascinating reaction manifold. Great stuff from Mihai, Nick, Zhuqing and Pearse!

An energy transfer mediated 4π spirocyclization intercepts the Staudinger β-lactam synthesis
ChemRxiv: DOI: 10.26434/chemrxiv-2023-kn7gf

Our latest paper is a practical guide to the determination of rotational barriers in atropisomers. A great collaboration with the Jonathan Clayden and Roly Armstrong groups.

Interrogating the Configurational Stability of Atropisomers
Nature Protocols: DOI: 10.1038/s41596-023-00859-y

Our latest preprint (a collaboration with the Paton group) shows how a new reaction manifold - radical-polar crossover from a triplet alkene - is enabled by a liberated iodine radical functioning as a single electron oxidant. This leads to complex natural-product like scaffolds in a process mediated by visible light. Great stuff from Zac, Mihai, Juan and Jay

A radical-polar crossover approach to complex nitrogen heterocycles via the triplet state
ChemRxiv: DOI: 10.26434/chemrxiv-2023-pcv6m

Our latest preprint on aryne generation from oxonium ions (with the Paton & Burton groups) in now online - great stuff from Owen, Maddie and Viorel!

Harnessing triaryloxonium ions for aryne generation
ChemRxiv: DOI: 10.26434/chemrxiv-2023-5wwqd

Congratulations to Ben, Mihai, Pearse and Ji-Yuan whose collaborative project with the Paton group has now been published.

Catalytic enantioselective 6𝝿 photocylization of acrylanilides
J. Am. Chem. Soc. 2022, DOI:

Congratulations to Ricky, Xiangqian and Morgan, whose work on the enantioselective cross coupling of indoles and naphthols is now published.

Enantioselective synthesis of atropisomeric indoles via iron catalysed oxidative cross coupling
Nature Chem. 2022, DOI:

A new approach to axially chiral medium ring compounds with high levels of enantioselectivity: great work from Tudor and Ji-Yuan and an excellent collaboration with Tim Claridge

Counterion-mediated enantioconvergent synthesis of axially chiral medium rings
J. Am. Chem. Soc. 2022, 144, 14970-14797.

Our work on visible light mediated 6𝝿 cyclizations continues with some great work from Ben, Mihai and Pearce in this collaboration with the Paton group.

Catalytic enantioselective 6𝝿 photocyclization of acrylanilides
ChemRxiv, DOI: 10.26434/chemrxiv-2022-dnzbk

Congratulations to Owen, Mihai and Maddie, whose collaboration with the Burton and Paton groups on controlling stereogenicity at oxygen is now available as a preprint.

Control of stereogenic oxygen in a helically chiral oxonium ion
ChemRxiv, DOI: 10.26434/chemrxiv-2022-I5qms

Congratulations to Mihai and Yao, whose work with Juan from the Paton Group has just been published in Angewandte Chemie.

Visible Light Mediated Heterocycle Functionalization via Geometrically Interrupted [2+2] Cycloaddition
Angew Chem. Int. Ed. 2020, 59, 23020.

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