Skip to main content

Research Repository

Advanced Search

Dr Matthew Kitching's Outputs (23)

Conglomerate Crystallization in the Cambridge Structural Database (2020–2021) (2023)
Journal Article
Walsh, M. P., Barclay, J. A., Begg, C. S., Xuan, J., & Kitching, M. O. (2023). Conglomerate Crystallization in the Cambridge Structural Database (2020–2021). Crystal Growth and Design, 23(4), 2837-2837. https://doi.org/10.1021/acs.cgd.3c00019

Conglomerate crystals are materials capable of undergoing spontaneous resolution and were responsible for the discovery of molecular chirality. Their relevance to modern chemical and crystallographic sciences has been hindered by the difficulty in id... Read More about Conglomerate Crystallization in the Cambridge Structural Database (2020–2021).

Identifying a Hidden Conglomerate Chiral Pool in the CSD (2022)
Journal Article
Walsh, M. P., Barclay, J. A., Begg, C. S., Xuan, J., Johnson, N. T., Cole, J. C., & Kitching, M. O. (2022). Identifying a Hidden Conglomerate Chiral Pool in the CSD. JACS Au, 2(10), 2235-2250. https://doi.org/10.1021/jacsau.2c00394

Conglomerate crystallization is the spontaneous generation of individually enantioenriched crystals from a nonenantioenriched material. This behavior is responsible for spontaneous resolution and the discovery of molecular chirality by Pasteur. The p... Read More about Identifying a Hidden Conglomerate Chiral Pool in the CSD.

Supramolecular Recognition of Quaternary Phosphonium Cations (2021)
Journal Article
Walsh, M. P., & Kitching, M. O. (2022). Supramolecular Recognition of Quaternary Phosphonium Cations. Crystal Growth and Design, 22(1), 251-258. https://doi.org/10.1021/acs.cgd.1c00887

The modes of supramolecular recognition of quaternary phosphonium cations mediated by 1,1′-bi-2-naphthol (BINOL) are identified and characterized. In contrast to our previous work on ammonium cations, the recognition of the quaternary phosphonium cat... Read More about Supramolecular Recognition of Quaternary Phosphonium Cations.

Enantioselective synthesis of ammonium cations (2021)
Journal Article
Walsh, M. P., Phelps, J. M., Lennon, M. E., Yufit, D. S., & Kitching, M. O. (2021). Enantioselective synthesis of ammonium cations. Nature, 597(7874), 70-76. https://doi.org/10.1038/s41586-021-03735-5

Control of molecular chirality is a fundamental challenge in organic synthesis. Whereas methods to construct carbon stereocentres enantioselectively are well established, routes to synthesize enriched heteroatomic stereocentres have garnered less att... Read More about Enantioselective synthesis of ammonium cations.

Regioselective Functionalization of 7‐Azaindole by Controlled Annular Isomerism: The Directed Metalation‐Group Dance (2019)
Journal Article
Snieckus, V., Patel, J., Kitching, M., Dalziel, M., Cosman, J., & Kaye, M. (2019). Regioselective Functionalization of 7‐Azaindole by Controlled Annular Isomerism: The Directed Metalation‐Group Dance. Angewandte Chemie, 131(22), 7391-7395. https://doi.org/10.1002/ange.201901724

The regioselective functionalization of 7‐azaindole by controlled annular directed metalation group isomerism is reported. The N‐7 carbamoyl azaindoles 2a–b undergo regioselective metalation and electrophile quench to furnish C‐6 substituted derivati... Read More about Regioselective Functionalization of 7‐Azaindole by Controlled Annular Isomerism: The Directed Metalation‐Group Dance.

Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by in situ Directing Group Generation (2018)
Journal Article
Snieckus, V., Kitching, M., Laars, M., Board, J., Patel, J., & Gan, W. (2018). Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by in situ Directing Group Generation. Angewandte Chemie, 130(30), 9569-9573. https://doi.org/10.1002/ange.201805203

A general synthesis of highly substituted 2‐naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with LiNE... Read More about Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by in situ Directing Group Generation.

Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group (2018)
Journal Article
Patel, J. J., Laars, M., Gan, W., Board, J., Kitching, M. O., & Snieckus, V. (2018). Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group. Angewandte Chemie International Edition, 57(30), 9425-9429. https://doi.org/10.1002/anie.201805203

A general synthesis of highly substituted 2‐naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with eith... Read More about Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group.

Flow-Assisted Synthesis: A Key Fragment of SR 142948A (2017)
Journal Article
Kitching, M. O., Dixon, O. E., Baumann, M., & Baxendale, I. R. (2017). Flow-Assisted Synthesis: A Key Fragment of SR 142948A. European Journal of Organic Chemistry, 2017(44), 6540-6553. https://doi.org/10.1002/ejoc.201700904

We report a series of multi-step flow operations to deliver an advanced hydrazine intermediate used in the assembly of the neurotensin modulator SR 142948A. Several new reactor configurations have enabled chemical transformations that would be otherw... Read More about Flow-Assisted Synthesis: A Key Fragment of SR 142948A.

Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine (2017)
Journal Article
De Bo, G., Gall, M. A., Kitching, M. O., Kuschel, S., Leigh, D. A., Tetlow, D. J., & Ward, J. W. (2017). Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine. Journal of the American Chemical Society, 139(31), 10875-10879. https://doi.org/10.1021/jacs.7b05850

We report on the synthesis and operation of a three-barrier, rotaxane-based, artificial molecular machine capable of sequence-specific β-homo (β3) peptide synthesis. The machine utilizes nonproteinogenic β3-amino acids, a class of amino acids not gen... Read More about Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine.

Tying a Molecular Overhand Knot of Single Handedness and Asymmetric Catalysis with the Corresponding Pseudo-D-3-Symmetric Trefoil Knot (2016)
Journal Article
Gil-Ramirez, G., Hoekman, S., Kitching, M. O., Leigh, D. A., Vitorica-Yrezabal, I. J., & Zhang, G. (2016). Tying a Molecular Overhand Knot of Single Handedness and Asymmetric Catalysis with the Corresponding Pseudo-D-3-Symmetric Trefoil Knot. Journal of the American Chemical Society, 138(40), 13159-13162. https://doi.org/10.1021/jacs.6b08421

We report the stereoselective synthesis of a left-handed trefoil knot from a tris(2,6-pyridinedicarboxamide) oligomer with six chiral centers using a lanthanide(III) ion template. The oligomer folds around the lanthanide ion to form an overhand knot... Read More about Tying a Molecular Overhand Knot of Single Handedness and Asymmetric Catalysis with the Corresponding Pseudo-D-3-Symmetric Trefoil Knot.

Metal-Free Synthesis of Dibenzoxazepinones via a One-Pot SNAr and Smiles Rearrangement Process: Orthogonality with Copper-Catalyzed Cyclizations (2015)
Journal Article
Hurst, T. E., Kitching, M. O., da Frota, L. C., Guimaraes, K. G., Dalziel, M. E., & Snieckus, V. (2015). Metal-Free Synthesis of Dibenzoxazepinones via a One-Pot SNAr and Smiles Rearrangement Process: Orthogonality with Copper-Catalyzed Cyclizations. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 26(11), 1455-1460. https://doi.org/10.1055/s-0034-1378839

The synthesis of neurotensin antagonist SR 48692 for prostate cancer research (2013)
Journal Article
Baxendale, I., Cheung, S., Kitching, M., Ley, S., & Shearman, J. (2013). The synthesis of neurotensin antagonist SR 48692 for prostate cancer research. Bioorganic and Medicinal Chemistry, 21(14), 4378-4387. https://doi.org/10.1016/j.bmc.2013.04.075

An improved synthesis of the molecule SR 48692 is presented and its use as a neurotensin antagonist biological probe for use in cancer research is described. The preparation includes an number of enhanced chemical conversions and strategies to overco... Read More about The synthesis of neurotensin antagonist SR 48692 for prostate cancer research.

A Machine-Assisted Flow Synthesis of SR48692: A Probe for the Investigation of Neurotensin Receptor-1 (2013)
Journal Article
Battilocchio, C., Deadman, B. J., Nikbin, N., Kitching, M. O., Baxendale, I. R., & Ley, S. V. (2013). A Machine-Assisted Flow Synthesis of SR48692: A Probe for the Investigation of Neurotensin Receptor-1. Chemistry - A European Journal, 19(24), 7917-7930. https://doi.org/10.1002/chem.201300696

Here we report the direct comparison of a conventional batch mode synthesis of Meclinertant (SR48692, 1), a neurotensin receptor-1 antagonist, with its machine-assisted flow chemistry alternative. By using these enabling tools, combined with solid-su... Read More about A Machine-Assisted Flow Synthesis of SR48692: A Probe for the Investigation of Neurotensin Receptor-1.

A Flow-Based Synthesis of 2-Aminoadamantane-2-carboxylic Acid (2012)
Journal Article
Battilocchio, C., Baxendale, I. R., Biava, M., Kitching, M. O., & Ley, S. V. (2012). A Flow-Based Synthesis of 2-Aminoadamantane-2-carboxylic Acid. Organic Process Research and Development, 16(5), 798-810. https://doi.org/10.1021/op300084z

The development of a new, high-yielding, scalable and safe process for the preparation of 2-aminoadamantane-2-carboxylic acid (1) is described. This geminal, functionalized achiral amino acid has been reported to possess interesting biological activi... Read More about A Flow-Based Synthesis of 2-Aminoadamantane-2-carboxylic Acid.

Scale-Up of Flow-Assisted Synthesis of C-2-Symmetric Chiral PyBox Ligands (2012)
Journal Article
Battilocchio, C., Baumann, M., Baxendale, I. R., Biava, M., Kitching, M. O., Ley, S. V., …Tappin, N. D. (2012). Scale-Up of Flow-Assisted Synthesis of C-2-Symmetric Chiral PyBox Ligands. Synthesis: Journal of Synthetic Organic Chemistry, 44(4), 635-647. https://doi.org/10.1055/s-0031-1289676

A series of PyBox ligands were prepared from commercially available chelidonic acid by a multistep flow sequence using mesoreactor technology. A chloro group introduced onto the ligand scaffold was subsequently exploited to give amine derivatives rea... Read More about Scale-Up of Flow-Assisted Synthesis of C-2-Symmetric Chiral PyBox Ligands.

Enzymatic Oxidative Cyclisation Reactions Leading to Dibenzoazocanes (2010)
Journal Article
Tozzi, F., Ley, S. V., Kitching, M. O., & Baxendale, I. R. (2010). Enzymatic Oxidative Cyclisation Reactions Leading to Dibenzoazocanes. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 2010(13), 1919-1922. https://doi.org/10.1055/s-0030-1258486

From simple N-isovanillyltyramine derivatives double oxidative biotransformations can be achieved using tyrosinase leading to the corresponding hydroxylated dibenzoazocanes.