alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

Research output

Research output per year 2014 2015 2017 2018 2021

• 20 Article (Academic Journal)
• 1 Special issue (Academic Journal)

Research output per year

Research output per year

Search results

• 2021

  N-Methyl Allylic Amines from Allylic Alcohols by Mitsunobu Substitution Using N-Boc Ethyl Oxamate

  Van Veen, B. C., Wales, S. M. & Clayden, J., 18 Jun 2021, In: Journal of Organic Chemistry. 86, 12, p. 8538-8543 6 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  • Ethyl 100%
  • Allylic Alcohol 100%
  • Oxamate 100%
  • Enantiopurity 50%
  • Primary Allylic Alcohol 50%
  4 Citations (Scopus)
• 2018

  Asymmetric α-Arylation of Amino Acids

  Leonard, D. J., Ward, J. W. & Clayden, J., 4 Oct 2018, In: Nature. 562, 7725, p. 105-109 5 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Amino Acids 100%
  • Arylation 100%
  • Amino Acid 100%
  • Precursor 66%
  • Enantiopurity 22%
  96 Citations (Scopus)

  842 Downloads (Pure)

• Chemoenzymatic Synthesis of Substituted Azepanes by Sequential Biocatalytic Reduction and Organolithium-Mediated Rearrangement

  Zawodny, W., Montgomery, S. L., Marshall, J. R., Finnigan, J. D., Turner, N. J. & Clayden, J., 26 Dec 2018, In: Journal of the American Chemical Society. 140, 51, p. 17872–17877 6 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Benzazepine Derivative 100%
  • Base 100%
  • Amine Oxidase (Flavin Containing) 100%
  • Imine 100%
  • Azepane 100%
  58 Citations (Scopus)

  312 Downloads (Pure)

• Consecutive Ring Expansion and Contraction for the Synthesis of 1-Aryl Tetrahydroisoquinolines and Tetrahydrobenzazepines from Readily Available Heterocyclic Precursors

  Hill, J. E., Matlock, J. V., Lefebvre, Q., Cooper, K. G. & Clayden, J., 14 May 2018, In: Angewandte Chemie - International Edition. 57, 20, p. 5788-5791 4 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Ring Expansion 100%
  • Ring Contraction 100%
  • Heterocyclic Compound 100%
  • Elimination Reaction 50%
  • Insertion Reaction 50%
  27 Citations (Scopus)

  412 Downloads (Pure)

• Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

  Mas-Roselló, J., Okoh, M. & Clayden, J., 7 Oct 2018, In: Chemical Communications. 54, 78, p. 10985-10988 4 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Nitrile 100%
  • Lithiation 33%
  • Chiral Auxiliary 33%
  • Phenytoin 33%
  9 Citations (Scopus)

  297 Downloads (Pure)

• Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas

  Hill, J. E., Lefebvre, Q., Fraser, L. A. & Clayden, J., 21 Sept 2018, In: Organic Letters. 20, 18, p. 5770-5773 4 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Tryptamine 100%
  • Indole 100%
  • Indolines 100%
  • Base 50%
  • Urea Derivative 50%
  16 Citations (Scopus)

  410 Downloads (Pure)

• Substituted Dihydroisoquinolinones by Iodide-Promoted Cyclocarbonylation of Aromatic α-Amino Acids

  Amer, M. M., Carrasco, A. C., Leonard, D. J., Ward, J. W. & Clayden, J., 21 Dec 2018, In: Organic Letters. 20, 24, p. 7977-7981 5 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Aromatic Amino Acid 100%
  • Lactam 100%
  • Cyclocarbonylation 100%
  • Imidazolidinone 50%
  • Bischler-Napieralski Reaction 50%
  16 Citations (Scopus)

  294 Downloads (Pure)

• Transition Metal Free Cycloamination of Prenyl Carbamates and Ureas Promoted by Aryldiazonium Salts

  Abrams, R., Lefebvre, Q. & Clayden, J., 8 Oct 2018, In: Angewandte Chemie - International Edition. 57, 41, p. 13587-13591 5 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Carbamates 100%
  • Transition Metal 100%
  • Ambient Reaction Temperature 33%
  • Ground State 33%
  • Cyclic Voltammetry 33%
  28 Citations (Scopus)

  379 Downloads (Pure)

• α-Methyl phenylglycines by asymmetric α-arylation of alanine and their effect on the conformational preference of helical Aib foldamers

  Costil, R., Fernández-Nieto, F., Atkinson, R. C. & Clayden, J., 21 Apr 2018, In: Organic and Biomolecular Chemistry. 16, 15, p. 2757-2761 5 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Arylation 100%
  • Oligomer 100%
  • Alanine 100%
  • NMR Spectroscopy 33%
  • Chiral Auxiliary 33%
  5 Citations (Scopus)

  375 Downloads (Pure)
• 2017

  Geometry-Retentive C-Alkenylation of Lithiated α-Aminonitriles: Quaternary α-Alkenyl Amino Acids and Hydantoins

  Mas-Roselló, J., Hachisu, S. & Clayden, J., 28 Aug 2017, In: Angewandte Chemie - International Edition. 56, 36, p. 10750-10754 5 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Alkene 100%
  • Alkenylation 100%
  • Hydantoin 100%
  • Amino Acid 100%
  • Carbon Atom 25%
  14 Citations (Scopus)

  452 Downloads (Pure)

• Heavily Substituted Atropisomeric Diarylamines by Unactivated Smiles Rearrangement of N-Aryl Anthranilamides

  Costil, R., Dale, H. J. A., Fey, N., Whitcombe, G., Matlock, J. V. & Clayden, J., 6 Sept 2017, (E-pub ahead of print) In: Angewandte Chemie - International Edition. 56, 41, p. 12533-12537 5 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Smiles Rearrangement 100%
  • Steric Hindrance 50%
  • Atropisomerism 50%
  • Enantiomer 50%
  54 Citations (Scopus)

  555 Downloads (Pure)

• Intramolecular vinylation of carbanions using N-acyl benzomorpholines as masked vinylureas and vinylcarbamates

  Corbet, B., Matlock, J., Mas Rosello, J. & Clayden, J., 1 Jun 2017, In: Comptes Rendus Chimie. 20, 6, p. 634-642 9 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Carbanion 100%
  • Carbamates 100%
  • vinylation 100%
  • Carbamic Acid 100%
  • Local-Density Approximation 50%
  7 Citations (Scopus)

  346 Downloads (Pure)

• Medium-Sized-Ring Analogues of Dibenzodiazepines by a Conformationally Induced Smiles Ring Expansion

  Costil, R., Lefebvre, Q. & Clayden, J., 16 Oct 2017, (E-pub ahead of print) In: Angewandte Chemie - International Edition. 56, 46, p. 14602-14606

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Ring Expansion 100%
  • Heterocyclic Compound 100%
  • Hydrophilicity 50%
  • Ground State 50%
  • Steric Hindrance 50%
  64 Citations (Scopus)

  497 Downloads (Pure)

• Stereospecific Intramolecular Arylation of 2- and 3-Pyridyl Substituted Alkylamines via Configurationally Stable α-Pyridyl Organolithiums

  Maury, J., Zawodny, W. & Clayden, J., 3 Feb 2017, In: Organic Letters. 19, 3, p. 472-475 4 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  Open Access

  File

  • Arylation 100%
  • Alkylamine 100%
  • Base 100%
  • Aliphatic Amine 100%
  • Substitution Reaction 50%
  14 Citations (Scopus)

  508 Downloads (Pure)
• 2016

  Medium-Ring Nitrogen Heterocycles through Migratory Ring Expansion of Metalated Ureas

  Hall, J., Matlock, J., Ward, J., Gray, K. V. & Clayden, J., 5 Sept 2016, In: Angewandte Chemie - International Edition. 55, 37, p. 11153-11157 5 p.

  Research output: Contribution to journal › Special issue (Academic Journal) › peer-review

  Open Access

  File

  • Ring Expansion 100%
  • Heterocyclic Compound 100%
  • Diastereoselectivity 33%
  • Benzodiazepine 33%
  • Deprotonation 33%
  97 Citations (Scopus)

  624 Downloads (Pure)
• 2015

  2,2- and 2,6-diarylpiperidines by aryl migration within lithiated urea derivatives of tetrahydropyridines

  Tait, M. B., Butterworth, S. & Clayden, J., 6 Mar 2015, In: Organic Letters. 17, 5, p. 1236-1239 4 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  • Tetrahydropyridine 100%
  • Chemistry 50%
  • Lithiation 50%
  • Piperidine 50%
  • Metalation 50%
  33 Citations (Scopus)

• Lithium choreography determines contrasting stereochemical outcomes of aryl migrations in benzylic carbamates, ureas and thiocarbamates

  Vincent, M. A., Maury, J., Hillier, I. H. & Clayden, J., 9 Feb 2015, In: European Journal of Organic Chemistry. 2015, 5, p. 953-959 7 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  • Lithium 100%
  • Carbamates 100%
  • Carbanion 50%
  • Potential Energy Surface 25%
  • Arylation 25%
  22 Citations (Scopus)

• Palladium Catalyzed C-Arylation of Amino Acid Derived Hydantoins

  Fernández-Nieto, F., Mas Roselló, J., Lenoir, S., Hardy, S. & Clayden, J., 7 Aug 2015, In: Organic Letters. 17, 15, p. 3838-3841 4 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  • Arylation 100%
  • Palladium 100%
  • Hydantoin 100%
  • Amino Acid 100%
  • Hydantoin Derivative 100%
  28 Citations (Scopus)

• Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives

  Atkinson, R. C., Fernández-Nieto, F., Mas Rosellõ, J. & Clayden, J., 27 Jul 2015, In: Angewandte Chemie - International Edition. 54, 31, p. 8961-8965 5 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  • Arylation 100%
  • Amino Acid Derivative 100%
  • Pseudoephedrine 100%
  • Amino Acid 100%
  • Hydantoin 50%
  52 Citations (Scopus)

• α-Quaternary Proline Derivatives by Intramolecular Diastereoselective Arylation of N-Carboxamido Proline Ester Enolates

  Maury, J. & Clayden, J., 6 Nov 2015, In: Journal of Organic Chemistry. 80, 21, p. 10757-10768 12 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  • Proline Derivative 100%
  • Enolates 100%
  • Arylation 100%
  • Proline 100%
  • Hydantoin Derivative 100%
  23 Citations (Scopus)
• 2014

  Synthesis of 1-arylcycloalkenamines by intramolecular arylation of lithiated ureas

  Tait, M. B., Ottersbach, P. A., Tetlow, D. J. & Clayden, J., 17 Oct 2014, In: Organic Process Research & Development. 18, 10, p. 1245-1252 8 p.

  Research output: Contribution to journal › Article (Academic Journal) › peer-review

  • Deprotonation 100%
  • Arylation 100%
  9 Citations (Scopus)