Developing Catalysis Research: New Reaction Discoveries and Practical Applications

Research output

Research output per year 2016 2017 2018 2019 2020 2022

• 38 Article
• 2 Review article
• 1 Literature review

Research output per year

Research output per year

Search results

• 2022

  Scope, limitations and mechanistic analysis of the HyperBTM-catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols

  Smith, S., Greenhalgh, M. D., Feoktistova, T., Walden, D. M., Taylor, J. E., Cordes, D. B., Slawin, A. M. Z., Cheong, P.H.-Y. & Smith, A. D., 11 Jan 2022, In: European Journal of Organic Chemistry. p. 30-43 14 p., e202101111.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Heterocyclic Compound 100%
  • Tertiary Alcohol 50%
  • Kinetic Method 50%
  • Methanol 50%
  • Enantiomer 50%
• 2021

  Catalytic enantioselective synthesis of 1,4-dihydropyridines via the addition of C(1)-ammonium enolates to pyridinium salts

  McLaughlin, C., Bitai, J., Barber, L., Slawin, A. & Smith, A. D., 6 Aug 2021, (E-pub ahead of print) In: Chemical Science. Advance Article, 11 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Enantioselectivity 100%
  • Pyridinium Salt 100%
  • Enolates 100%
  • Base 50%
  • Organocatalysis 50%

• Enantioselective synthesis of α-aryl-β²-amino-esters by cooperative isothiourea and Brønsted acid catalysis

  Zhao, F., Shu, C., Young, C. M., Carpenter-Warren, C., Slawin, A. M. Z. & Smith, A. D., 11 May 2021, In: Angewandte Chemie International Edition. 60, 21, p. 11892-11900 10 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Acid Catalysis 100%
  • pre-catalyst 100%
  • Ammonium Ion 50%
  • Mechanistic Study 50%
  • Iminium Ion 50%

• Isothiourea-catalyzed enantioselective α-alkylation of esters via 1,6-conjugate addition to para-quinone methides

  Arokianathar, J. N., Hartley, W., McLaughlin, C., Greenhalgh, M. D., Stead, D., Ng, S., Slawin, A. M. Z. & Smith, A. D., 20 Oct 2021, In: Molecules. 26, 21, 13 p., 6333.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Quinone 100%
  • Alkylation 100%
  • Carboxamide 50%
  • Benzylamine 50%
  • N-acylation 50%
• 2020

  Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives

  Bitai, J., Slawin, A. M. Z., Cordes, D. B. & Smith, A. D., 25 May 2020, In: Molecules. 25, 10, 13 p., 2463.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Amino Acid Derivative 100%
  • Palladium 100%
  • Carboxamide 50%
  • N,N-Dimethylglycine 50%
  • Quaternary Ammonium Salt 50%

• Generation and reactivity of C(1)-ammonium enolates using isothiourea catalysis

  McLaughlin, C. & Smith, A. D., 10 Nov 2020, (E-pub ahead of print) In: Chemistry - A European Journal. Early View

  Research output: Contribution to journal › Review article › peer-review

  Open Access

  File

  • Enolates 100%
  • Carboxylic Acid 66%
  • Imidazole 33%
  • Electrophile 33%
  • Halide 33%

• Isothiourea-catalyzed acylative kinetic resolution of tertiary α-hydroxy esters

  Qu, S., Smith, S., Laina-Martin, V., Neyyappadath, R., Greenhalgh, M. D. & Smith, A. D., 14 Sept 2020, In: Angewandte Chemie International Edition. 59, 38, p. 16572-16578 8 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Tertiary Alcohol 100%
  • Enantioselectivity 100%
  • Diastereomer 50%
  • Methanol 50%
  • Transition State 50%

• Isothiourea-catalyzed atropselective acylation of biaryl phenols via sequential desymmetrization/kinetic resolution

  Munday, E. S., Grove, M., Feoktistova, T., Brueckner, A. C., Walden, D., Young, C. M., Slawin, A. M. Z., Campbell, A., Cheong, P.H.-Y. & Smith, A. D., 11 Mar 2020, (E-pub ahead of print) In: Angewandte Chemie International Edition. Early View

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Biaryl 100%
  • Acylation 100%
  • Diol 75%
  • Enantiopurity 25%
  • Natural Product 25%

• Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones

  Liu, H., Slawin, A. M. M. & Smith, A. D., 6 Feb 2020, (E-pub ahead of print) In: Organic Letters. Articles ASAP

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Base Catalyst 100%
  • Imine 100%
  • Enantioselectivity 100%
  • Ring Formation 100%
  • Lewis Base 100%

• Isothiourea-catalyzed functionalization of pyrrolyl- and indolylacetic acid: enantioselective synthesis of dihydropyridinones and one-pot synthesis of pyridinones

  Zhang, S., Bacheley, L., Young, C. M., Stark, D. G., O'Riordan, T., Slawin, A. M. Z. & Smith, A. D., Oct 2020, In: Asian Journal of Organic Chemistry. 9, 10, p. 1562-1566 5 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Imidazole 100%
  • One Pot Reaction 100%
  • Ketimine 100%
  • Indole 100%
  • Pyrrole 100%

• Isothiourea-catalyzed transfer hydrogenation of α,β-unsaturated para-nitrophenyl esters

  Wu, J., Young, C. M. & Smith, A. D., 13 Nov 2020, (E-pub ahead of print) In: Tetrahedron. In press, 131758.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Hydrogenation 100%
  • Carboxamide 50%
  • Methyl Ester 50%
  • Nucleophile 50%

• Recent developments in enantioselective photocatalysis

  Prentice, C., Morrisson, J., Smith, A. D. & Zysman-Colman, E., 29 Sept 2020, In: Beilstein Journal of Organic Chemistry. 2020, 16, p. 2363-2441 79 p.

  Research output: Contribution to journal › Literature review › peer-review

  Open Access

  File

  • Photocatalysis 100%
  • Enantioselective Catalysis 33%

• Tandem sequential catalytic enantioselective synthesis of highly-functionalised tetrahydroindolizine derivatives

  Zhang, S., Greenhalgh, M. D., Slawin, A. M. Z. & Smith, A. D., 12 Mar 2020, (E-pub ahead of print) In: Chemical Science. Advance Article, 8 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Michael Addition 100%
  • Ring Opening Reaction 100%
  • Enone 100%
  • Acetic Acid 100%
  • lactonization 100%
• 2019

  Base-free enantioselective C(1)-ammonium enolate catalysis exploiting aryloxides: a synthetic and mechanistic study

  McLaughlin, C., Slawin, A. M. Z. & Smith, A. D., 14 Oct 2019, In: Angewandte Chemie International Edition. 58, 42, p. 15111-15119 9 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Mechanistic Study 100%
  • Michael Addition 100%
  • Base 100%
  • Enolates 100%
  • Stereoselectivity 50%

• Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones via a concerted asynchronous [2+2] cycloaddition: a synthetic and computational study

  Barrios Antunez, D.-J., Greenhalgh, M. D., Brueckner, A. C., Walden, D. M., Elías-Rodríguez, P., Roberts, P., Young, B. G., West, T. H., Slawin, A. M. Z., Cheong, P.H.-Y. & Smith, A. D., 28 Jun 2019, In: Chemical Science. 10, 24, p. 6162-6173 12 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Lactone 100%
  • Cycloaddition 100%
  • Ketones 50%
  • 1,2-cycloaddition 25%
  • Anhydride 25%

• Evaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonisations

  Young, C. M., Taylor, J. E. & Smith, A. D., 21 May 2019, In: Organic & Biomolecular Chemistry. 17, 19, p. 4747-4752

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Michael Addition 100%
  • Enolates 100%
  • Stereoselectivity 50%
  • Ring Opening Reaction 50%
  • Diester 50%

• Isothiourea-catalysed enantioselective Michael addition of N-heterocyclic pronucleophiles to α,β-unsaturated aryl esters

  Shu, C., Liu, H., Slawin, A., Carpenter-Warren, C. L. & Smith, A. D., 23 Oct 2019, (E-pub ahead of print) In: Chemical Science. Advance Article, 7 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Michael Addition 100%
  • Heterocyclic Compound 100%
  • Tertiary Amine 50%
  • Enantioselectivity 50%
  • Lewis Base 50%

• Isothiourea-catalysed regioselective acylative kinetic resolution of axially chiral biaryl diols

  Qu, S., Greenhalgh, M. D. & Smith, A. D., 28 Jan 2019, (E-pub ahead of print) In: Chemistry - A European Journal. Early View

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Biaryl 100%
  • Diol 100%
  • Anhydride 50%
  • Acylation 50%
  • Transition State 25%

• Isothiourea-catalysed sequential kinetic resolution of acyclic (±)-1,2-diols

  Harrer, S., Greenhalgh, M. D., Neyyappadath, R. M. & Smith, A. D., Aug 2019, In: Synlett. 30, 13, p. 1555-1560

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Diol 100%

• NHC-catalysed enantioselectiveintramolecular formal [4+2] cycloadditions using carboxylic acids as azolium enolate precursors

  Attaba, N. & Smith, A. D., 6 Dec 2019, (E-pub ahead of print) In: Tetrahedron. In press

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Enantioselectivity 100%
  • Cycloaddition 100%
  • Enolates 100%
  • Diastereoselectivity 100%
  • Carboxylic Acid 100%

• Synthesis of fused indoline-cyclobutanone derivatives via an intramolecular [2+2] cycloaddition

  Neyyappadath, R. M., Greenhalgh, M. D., Cordes, D. B., Slawin, A. M. Z. & Smith, A. D., 12 Apr 2019, (E-pub ahead of print) In: European Journal of Organic Chemistry. Early View

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Ketene 100%
  • Cycloaddition 100%
  • Indoline 100%
  • Base Catalysis 33%
  • Cyclic Structure 33%

• Unanticipated silyl transfer in enantioselective α,β-unsaturated acyl ammonium catalysis using silyl nitronates

  Matviitsuk, A., Greenhalgh, M. D., Taylor, J. E., Nguyen, X. B., Cordes, D. B., Slawin, A. M. Z., Lupton, D. W. & Smith, A. D., 23 Dec 2019, (E-pub ahead of print) In: Organic Letters. Article ASAP

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Silyl 100%
  • formation 20%
  • Enantioselectivity 20%
• 2018

  A C=O•••isothiouronium interaction dictates enantiodiscrimination in acylative kinetic resolution of tertiary heterocyclic alcohols

  Greenhalgh, M. D., Smith, S. M., Walden, D. M., Taylor, J. E., Brice, Z., Robinson, E. R. T., Fallan, C., Cordes, D. B., Slawin, A. M. Z., Richardson, H. C., Grove, M. A., Cheong, P.H.-Y. & Smith, A. D., 12 Mar 2018, In: Angewandte Chemie International Edition. 57, 12, p. 3200-3206 7 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Heterocyclic Compound 100%
  • Methanol 33%
  • Acetic Anhydride 33%

• Acylative kinetic resolution of alcohols using a recyclable polymer-supported isothiourea catalyst in batch and flow

  Neyyappadath, R., Chisholm, R., Greenhalgh, M. D., Rodriguez-Escrich, C., Pericàs, M. A., Hähner, G. & Smith, A. D., 2 Feb 2018, In: ACS Catalysis. 8, 2, p. 1067-1075 9 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Anhydride 100%
  • Diol 50%
  • Base Catalyst 50%
  • Homogeneous Catalyst 50%
  • Secondary Alcohol 50%

• Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions

  Greenhalgh, M. D., Taylor, J. E. & Smith, A. D., 20 Sept 2018, In: Tetrahedron. 74, 38, p. 5554-5560 7 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Best Practice 100%
  • Metrics 100%
  • High-Performance Liquid Chromatography 100%
  • High Performance Liquid Chromatography 100%
  • Selectivity 100%

• Chiral Au^I- and Au^III-isothiourea complexes: synthesis, characterization and application

  Gasperini, D., Greenhalgh, M., Imad, R., Siddiqui, S., Malik, A., Arshad, F., Choudhary, M. I., Al-Majid, A., Cordes, D., Slawin, A., Nolan, S. & Smith, A. D., 21 Dec 2018, (E-pub ahead of print) In: Chemistry - A European Journal. Early View

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Enantiopurity 100%
  • Catalyst Activity 100%
  • Iridium 100%
  • formation 100%
  • Organocatalysis 100%

• Evaluating polymer-supported isothiourea catalysis in industrially-preferable solvents for the acylative kinetic resolution of secondary and tertiary heterocyclic alcohols in batch and flow

  Guha, N., Neyya Ppadath, R. M., Greenhalgh, M., Chisholm, R., Smith, S., McEvoy, M., Rodríguez-Escrich, C., Young, C. M., Pericas, M. A., Hähner, G. & Smith, A. D., 24 Aug 2018, (E-pub ahead of print) In: Green Chemistry. In press

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Heterocyclic Compound 100%
  • Dimethyl Carbonate 25%
  • Packed Bed Reactor 25%
  • Immobilized Catalyst 25%
  • Base Catalyst 25%

• Isothiourea-catalyzed enantioselective addition of 4-nitrophenyl esters to iminium ions

  Arokianathar, J. N., Frost, A. B., Slawin, A. M. Z., Stead, D. & Smith, A. D., 2 Feb 2018, In: ACS Catalysis. 8, 2, p. 1153-1160

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Iminium Ion 100%
  • Enantioselectivity 100%
  • Carboxamide 50%
  • N-acylation 50%
  • Base Catalyst 50%

• Isothiourea-catalyzed enantioselective functionalization of 2-pyrrolyl acetic acid: two-step synthesis of stereodefined dihydroindolizinones

  Zhang, S., Taylor, J. E., Slawin, A. M. Z. & Smith, A. D., 24 Aug 2018, (E-pub ahead of print) In: Organic Letters. In press

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Acetic Acid 100%
  • Trichloromethyl(.) 50%
  • Benzylamine 50%
  • Ring Opening Reaction 50%
  • Methanol 50%

• Multiple roles of aryloxide leaving groups in enantioselective annulations employing α,β-unsaturated acyl ammonium catalysis

  Greenhalgh, M., Qu, S., Slawin, A. & Smith, A. D., 7 Jun 2018, In: Chemical Science. 9, 21, p. 4909-4918 10 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Isomerization 100%
  • Base 100%
  • Ring Formation 100%
  • Aryl Group 50%
  • Michael Addition 50%

• Selective and catalytic carbon dioxide and heteroallene activation mediated by cerium N-heterocyclic carbene complexes

  Arnold, P. L., Kerr, R. W. F., Weetman, C., Docherty , S. R., Rieb, J., Cruickshank, F. L., Wang, K., Jandl, C., McMullon, M. W., Pöthig, A., Kühn, F. E. & Smith, A. D., 10 Sept 2018, (E-pub ahead of print) In: Chemical Science. Advance Article, 11 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • N-Heterocyclic Carbene 100%
  • Cerium 100%
  • Carbon Dioxide 100%
  • Propene 33%
  • Isopropyl Group 33%
• 2017

  Aryloxide-facilitated catalyst turnover in enantioselective α,β-unsaturated acyl ammonium catalysis

  Matviitsuk, A., Greenhalgh, M., Barrios Antunez, D., Slawin, A. & Smith, A. D., 25 Sept 2017, In: Angewandte Chemie. 129, 40, p. 12450-12455 6 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Mechanistic Study 100%
  • Michael Addition 100%
  • Kinetic Method 100%
  • Complex Reaction Mechanisms 100%
  • Enantioselectivity 100%

• Aryloxide-promoted catalyst turnover in Lewis base organocatalysis

  Hartley, W. C., O'Riordan, T. J. C. & Smith, A. D., Aug 2017, In: Synthesis. 49, 15, p. 3303-3310

  Research output: Contribution to journal › Review article › peer-review

  Open Access

  File

  • Organocatalysis 100%
  • Lewis Base 100%
  • Cinchona Alkaloid 50%
  • Polypyrrole 50%
  • Tertiary Amine 50%

• Catalytic enantioselective [2,3]-rearrangements of allylic ammonium ylides: a mechanistic and computational study

  West, T. H., Walden, D. M., Taylor, J. E., Brueckner, A. C., Johnston, R. C., Cheong, P.H.-Y., Lloyd-Jones, G. C. & Smith, A. D., 29 Mar 2017, In: Journal of the American Chemical Society. 139, 12, p. 4366-4375 10 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Ammonium Ylide 100%
  • Mechanistic Study 50%
  • catalytic cycle 50%
  • Kinetic Method 50%
  • Density Functional Theory 50%

• Enantioselective NHC-catalysed redox [4+2]-hetero-Diels-Alder reactions using α-aroyloxyaldehydes and unsaturated ketoesters

  Taylor, J. E., Davies, A. T., Douglas, J. J., Churchill, G. & Smith, A. D., 15 Feb 2017, In: Tetrahedron: Asymmetry. 28, 2, p. 355-366

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • N-Heterocyclic Carbene 100%
  • Ketoester 100%
  • Hetero Diels-Alder Cycloaddition 100%
  • Diastereoselectivity 100%
  • Epimerization 25%

• Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines

  Kerr, R. W. F., Greenhalgh, M. D., Slawin, A. M. Z., Arnold, P. L. & Smith, A. D., 15 Jan 2017, In: Tetrahedron: Asymmetry. 28, 1, p. 125-134

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • N-Heterocyclic Carbene 100%
  • Oxaziridine 100%
  • Cycloaddition 100%
  • Mechanistic Study 33%
  • Enantioselectivity 33%

• Enantioselective synthesis of β-fluoro-β-aryl-α-amino pentenamides by organocatalytic [2,3]-sigmatropic rearrangement

  Kasten, K., Slawin, A. M. Z. & Smith, A. D., 6 Oct 2017, In: Organic Letters. 19, 19, p. 5182-5185 4 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Benzylamine 100%
  • Quaternary Ammonium Salt 100%
  • Fluorine 100%
  • Organocatalysis 100%
  • Tetramisole 100%

• Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides

  West, T. H., Spoehrle, S. S. M. & Smith, A. D., 20 Jul 2017, In: Tetrahedron. 73, 29, p. 4138-4149 12 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Chemoselectivity 100%
  • Ammonium Ylide 100%
  • Piperidine 100%

• Tandem palladium and isothiourea relay catalysis: enantioselective synthesis of α-amino acid derivatives via allylic amination and [2,3]-sigmatropic rearrangement

  Spoehrle, S. S. M., West, T. H., Taylor, J. E., Slawin, A. M. Z. & Smith, A. D., 30 Aug 2017, In: Journal of the American Chemical Society. 139, 34, p. 11895-11902 8 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Amino Acid Derivative 100%
  • Palladium 100%
  • Enantioselective Catalysis 100%
  • Allylic Amination 100%
  • Ethyl 33%
• 2016

  Enantioselective stereodivergent nucleophile-dependent isothiourea-catalysed domino reactions

  Matviitsuk, A., Taylor, J. E., Cordes, D. B., Slawin, A. M. Z. & Smith, A. D., 5 Dec 2016, In: Chemistry - A European Journal. 22, 49, p. 17748-17757 10 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Domino Reaction 100%
  • Nucleophile 100%
  • Stereoselectivity 33%
  • 2,4,6-trichlorophenol 33%
  • Enone 33%

• Isothiourea-catalysed enantioselective pyrrolizine synthesis: synthetic and computational studies

  Stark, D. G., Williamson, P., Gayner, E. R., Musolino, S. F., Kerr, R. W. F., Taylor, J. E., Slawin, A. M. Z., O'Riordan, T. J. C., Macgregor, S. A. & Smith, A. D., 14 Oct 2016, In: Organic & Biomolecular Chemistry. 14, 38, p. 8957-8965 9 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  File

  • Pyrrolizine 100%
  • Ring Opening Reaction 66%
  • Enone 66%
  • formation 33%
  • Enantioselectivity 33%