Outputs (33)

Sulfonimidates: useful synthetic intermediates for sulfoximine synthesis via C–S bond formation (2018)
Journal Article
Matos, P. M., Lewis, W., Moore, J. C., & Stockman, R. A. (2018). Sulfonimidates: useful synthetic intermediates for sulfoximine synthesis via C–S bond formation. Organic Letters, 20(12), 3674-3677. https://doi.org/10.1021/acs.orglett.8b01473

The ever-increasing prevalence of sulfoximine derivatives in drug discovery programmes has brought about a renaissance in the development of methods for their synthesis. Sulfoximine synthesis via C-S bond formation however has been comparatively unde... Read More about Sulfonimidates: useful synthetic intermediates for sulfoximine synthesis via C–S bond formation.

Exploration of novel chemical space: synthesis and in vitro evaluation of N-functionalized tertiary sulfonimidamides (2018)
Journal Article
Izzo, F., Schäfer, M., Lienau, P., Ganzer, U., Stockman, R., & Lücking, U. (2018). Exploration of novel chemical space: synthesis and in vitro evaluation of N-functionalized tertiary sulfonimidamides. Chemistry - A European Journal, 24(37), 9295-9304. https://doi.org/10.1002/chem.201801557

An unprecedented set of structurally diverse sulfonimidamides (47 compounds) has been prepared by various N‐functionalization reactions of tertiary =NH sulfonimidamide 2 aa. These N‐functionalization reactions of model compound 2 aa include arylation... Read More about Exploration of novel chemical space: synthesis and in vitro evaluation of N-functionalized tertiary sulfonimidamides.

A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides (2017)
Journal Article
Izzo, F., Schäfer, M., Stockman, R., & Lücking, U. (2017). A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides. Chemistry - A European Journal, 23(60), 15189-15193. https://doi.org/10.1002/chem.201703272

Unprotected tertiary sulfonimidamides have been prepared in good to excellent yields in a one‐pot transformation from tertiary sulfinamides through NH transfer. The reaction is mediated by commercially available (diacetoxyiodo)benzene and ammonium ca... Read More about A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides.

Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji–Trost Allylation of N-tert-Butanesulfinyl Imines (2017)
Journal Article
Dawood, R. S., Georgiou, I., Wilkie, R. P., Lewis, W., & Stockman, R. A. (2017). Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji–Trost Allylation of N-tert-Butanesulfinyl Imines. Chemistry - A European Journal, 23(46), 11153-11158. https://doi.org/10.1002/chem.201702616

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim A simple and efficient asymmetric synthesis of novel sp 3 -rich pyrrolidine chemical scaffolds over five steps starting from simple ketones is described. Key steps involve the use of tert-butanesul... Read More about Asymmetric Synthesis of Pyrrolidine-Containing Chemical Scaffolds via Tsuji–Trost Allylation of N-tert-Butanesulfinyl Imines.

Expedient synthesis of an atypical oxazolidinone compound library (2016)
Journal Article
Cully, S. J., Storr, T. E., Rawling, M. J., Abeysena, I. R., Hamza, D., Jones, G., Pearce, C. A., Quddus, A., Lewis, W., & Stockman, R. A. (2016). Expedient synthesis of an atypical oxazolidinone compound library. Bioorganic and Medicinal Chemistry, 24(21), 5249-5257. https://doi.org/10.1016/j.bmc.2016.08.046

In order to address the current downturn in the drug discovery pipeline, initiatives are being undertaken to synthesise screening libraries of sp3-rich, low molecular weight compounds. As part of the European Lead Factory initiative, the synthesis an... Read More about Expedient synthesis of an atypical oxazolidinone compound library.

Versatile C(sp2)−C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes (2016)
Journal Article
Dean, W. M., Mindaugas, Š., Storr, T. E., Lewis, W., & Stockman, R. A. (2016). Versatile C(sp2)−C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes. Angewandte Chemie International Edition, 55(34), 10013-10016. https://doi.org/10.1002/anie.201602264

The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98% yield and greater than 99.5% enantiomeric excess. This ligand coupling reaction is tolerant to multiple substitution... Read More about Versatile C(sp2)−C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes.

Versatile C(sp2)−C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes (2016)
Journal Article
Dean, W. M., Šiaučiulis, M., Storr, T. E., Lewis, W., & Stockman, R. A. (2016). Versatile C(sp2)−C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes. Angewandte Chemie, 128(34), 10167-10170. https://doi.org/10.1002/ange.201602264

The reaction of chiral (hetero)aryl benzyl sulfoxides with Grignard reagents affords enantiomerically pure diarylalkanes in up to 98 % yield and greater than 99.5 % enantiomeric excess. This ligand coupling reaction is tolerant to multiple substituti... Read More about Versatile C(sp2)−C(sp3) Ligand Couplings of Sulfoxides for the Enantioselective Synthesis of Diarylalkanes.

Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines (2016)
Journal Article
Moragas, T., Liffey, R. M., Regentova, D., Ward, J.-P., Dutton, J., Lewis, W., Churcher, I., Walton, L., Souto, J., & Stockman, R. A. (2016). Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines. Angewandte Chemie International Edition, 55(34), 10047-10051. https://doi.org/10.1002/anie.201604188

A novel rearrangement of 2-vinyl aziridine 2-carboxylates to unusual chiral cyclic sulfoximines is described herein. The method allows the synthesis of substituted cyclic sulfoximines in high yields with complete stereocontrol, displaying a wide sub... Read More about Sigmatropic Rearrangement of Vinyl Aziridines: Expedient Synthesis of Cyclic Sulfoximines from Chiral Sulfinimines.

A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings (2016)
Journal Article
Sainz, M. F., Souto, J. A., Regentova, D., Johansson, M. K. G., Timhagen, S. T., Irvine, D. J., Buijsen, P., Koning, C. E., Stockman, R. A., & Howdle, S. M. (2016). A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings. Polymer Chemistry, 7(16), 2882-2887. https://doi.org/10.1039/c6py00357e

We present new acrylic monomers derived directly from abundant naturally available terpenes via a facile, green and catalytic approach. These monomers can be polymerised to create new polymers with a wide range of mechanical properties that positions... Read More about A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings.

Facile access to a heterocyclic, sp3-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy (2015)
Journal Article
Rawling, M., Storr, T., Bawazir, W., Cully, S., Lewis, W., Makki, M., Strutt, I., Jones, G., Hamza, D., & Stockman, R. (2015). Facile access to a heterocyclic, sp3-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy. Chemical Communications, 51(64), https://doi.org/10.1039/c5cc05070g

A heterocyclic, sp3-rich chemical scaffold was synthesised in just 6 steps via a highly regio- and diastereo-selective tandem nitrone formation/intramolecular nitrone–alkene [3+2] cycloaddition reaction. A library of 543 lead-like compounds based on... Read More about Facile access to a heterocyclic, sp3-rich chemical scaffold via a tandem condensation/intramolecular nitrone–alkene [3+2] cycloaddition strategy.