Publications

Preprints

The Catalytic Enantioselective [1,2]-Wittig Rearrangement of Allylic Ethers
Tengfei Kang, Justin O’Yang, Kevin Kasten, Elliot H. E. Farrar, Samuel S. Allsop, Martin Juhl, David B. Cordes, Aidan P. McKay, Matthew N. Grayson,* and Andrew D. Smith*
ChemRxiv 2023

Published

49. Reformulating Reactivity Design for Data-Efficient Machine Learning
Toby Lewis-Atwell, Daniel Beechey, Özgür Şimşek, and Matthew N. Grayson*
ACS Catal. 2023, 13, 13506

48. Machine learning reaction barriers in low data regimes: a horizontal and diagonal transfer learning approach
Samuel G. Espley, Elliot H. E. Farrar, David Buttar, Simone Tomasi, and Matthew N. Grayson*
Digital Discovery 2023, 2, 941

47. Photoredox-HAT Catalysis for Primary Amine α-C–H Alkylation: Mechanistic Insight with Transient Absorption Spectroscopy
Mahima Sneha, Georgia L. Thornton, Luke Lewis-Borrell, Alison S. H. Ryder, Samuel G. Espley, Ian P. Clark, Alexander J. Cresswell, Matthew N. Grayson, and Andrew J. Orr-Ewing
ACS Catal. 2023, 13, 8004

46. Photochemical Fingerprinting Is a Sensitive Probe for the Detection of Synthetic Cannabinoid Receptor Agonists; toward Robust Point-of-Care Detection
Rachael C. Andrews, Benedict May, Federico J. Hernández, Gyles E. Cozier, Piers A. Townsend, Oliver B. Sutcliffe, Tom S. F. Haines, Tom P. Freeman, Jennifer Scott, Stephen M. Husbands, Ian S. Blagbrough, Richard W. Bowman, Simon E. Lewis, Matthew N. Grayson,* Rachel Crespo-Otero,* David R. Carbery,* and Christopher R. Pudney*
Anal. Chem. 2023, 95, 703

45. Atom and step economical synthesis of acyclic quaternary centers via iridium-catalyzed hydroarylative cross-coupling of 1,1-disubstituted alkenes
Phillippa Coope, Andrew G. Dalling, Elliot H. E. Farrar, Timothy P. Aldhous, Simon Grélaud, Eleanor Lester, Lyman J. Feron, Paul D. Kemmitt, Matthew N. Grayson,*  and  John F. Bower*
Chem. Sci. 2022, 13, 11183

44. B(C6F5)3-Catalyzed (E)-Selective Isomerization of Alkenes
Betty A. Kustiana, Salma A. Elsherbeni, Thomas G. Linford-Wood, Rebecca L. Melen, Matthew N. Grayson, and Louis C. Morrill
Chem. Eur. J. 2022, 28, e202202454

43. Eliminating Transition State Calculations for Faster and More Accurate Reactivity Prediction in Sulfa-Michael Additions Relevant to Human Health and the Environment
Piers A. Townsend, Elliot H. E. Farrar, and Matthew N. Grayson*
ACS Omega 2022, 7, 26945

42. Noncovalent Interactions in the Oxazaborolidine-Catalyzed Enantioselective Mukaiyama Aldol
Elliot H. E. Farrar and Matthew N. Grayson*
J. Org. Chem. 2022, 87, 10054

41. Machine learning and semi-empirical calculations: A synergistic approach to rapid, accurate, and mechanism-based reaction barrier prediction
Elliot H. E. Farrar and Matthew N. Grayson*
Chem. Sci. 2022, 13, 7594
Featured in the themed collection: Celebrating our 2023 Prizewinners

40. Comparing the Performances of Force Fields in Conformational Searching of Hydrogen-Bond-Donating Catalysts
Toby Lewis-Atwell, Piers A. Townsend, and Matthew N. Grayson*
J. Org. Chem. 2022, 87, 5703

39. Heteroatom-Tethered ω-Alkenylallylboronates: Stereoselective Synthesis of Heterocyclic Derived Alcohols
Francisco Garnes-Portolés, Rubén Miguélez, Matthew N. Grayson, and Pablo Barrio
Synthesis 2022, 54, 3817

38. The message on the bottle: Rethinking plastic labelling to better encourage sustainable use
Stephen D. Burrows, Francisca Ribeiro, Stacey O’Brien, Elvis Okoffo, Tania Toapanta, Nathan Charlton, Sarit Kaserzon, Chun-Yin Lin, Cheng Tang, Cassandra Rauert, Xianyu Wang, Katja Shimko, Jake O’Brien, Piers A. Townsend, Matthew N. Grayson, Tamara Galloway, and Kevin V. Thomas
Environ. Sci. Policy 2022, 132, 109

37. Organocatalytic Enantioselective Sulfa-Michael Additions to α,β-Unsaturated Diazoketones
Patricia B. Momo, Eduardo F. Mizobuchi, Radell Echemendía, Isabel Baddeley, Matthew N. Grayson*, and Antonio C. B. Burtoloso*
J. Org. Chem. 2022, 87, 3482

36. Iron-Catalyzed H/D Exchange of Primary Silanes, Secondary Silanes, and Tertiary Siloxanes
Thomas G. Linford-Wood, Mary F. Mahon, Matthew N. Grayson*, and Ruth L. Webster*
ACS Catal. 2022, 12, 2979

35. Machine Learning Activation Energies of Chemical Reactions
Toby Lewis-Atwell, Piers A. Townsend and Matthew N. Grayson*
Wiley Interdiscip. Rev. Comput. Mol. Sci. 2022, 12, e1593

34. Chiral Phosphoric Acid Catalysis: The Terada Model Revisited
Matthew N. Grayson*
J. Org. Chem. 2021, 86, 13631

33. A molecular communication channel consisting of a single reversible chain of hydrogen bonds in a conformationally flexible oligomer
David T. J. Morris, Steven M. Wales, David P. Tilly, Elliot H. E. Farrar, Matthew N. Grayson, John W. Ward and Jonathan Clayden
Chem, 2021, 7, 2460

32. ω-Alkenylallylboronates: Design, Synthesis and Application to the Asymmetric Allylation / RCM Tandem Sequence
Francisco Garnes-Portolés, Rubén Miguélez, Matthew N. Grayson and Pablo Barrio
Eur. J. Org. Chem., 2021, 24, 3492

31. Understanding the mechanism of the chiral phosphoric acid-catalyzed aza-Cope rearrangement
Bruno N. Falcone and Matthew N. Grayson*
Org. Biomol. Chem., 2021, 19, 3656
Featured in the themed collection: Celebrating our 2023 Prizewinners

30. Density Functional Theory in the Prediction of Mutagenicity: A Perspective
Piers A. Townsend and Matthew N. Grayson*
Chem. Res. Toxicol., 2021, 34, 179
Part of the Special Issue in Computational Toxicology

29. Control of Crystallinity and Stereocomplexation of Synthetic Carbohydrate Polymers from D‐ and L‐Xylose
Thomas M. McGuire, Jessica Bowles, Edward Deane, Elliot H. E. Farrar, Matthew N. Grayson and Antoine Buchard
Angew. Chem. Int. Ed., 2021, 60, 4524
Highlighted as Very Important Paper

28. Comparisons of Different Force Fields in Conformational Analysis and Searching of Organic Molecules: A Review
Toby Lewis-Atwell, Piers A. Townsend and Matthew N. Grayson*
Tetrahedron, 2021, 79, 131865 (special issue dedicated to the achievements of Prof Jonathan Williams)

27. Computational Studies of Chiral Hydroxyl Carboxylic Acids: The Allylboration of Aldehydes
Elliot H. E. Farrar and Matthew N. Grayson*
J. Org. Chem. 2020, 85, 15449

26. Reactivity Prediction in Aza-Michael Additions without Transition State Calculations: The Ames Test for Mutagenicity
Piers A. Townsend and Matthew N. Grayson*
Chem. Commun., 2020, 56, 13661

25. Enantioselective Total Synthesis of (–)-Finerenone using Asymmetric Transfer Hydrogenation
Andreas Lerchen, Narasimhulu Gandhamsetty, Elliot H. E. Farrar, Nils Winter, Johannes Platzek, Matthew N. Grayson* and Varinder K. Aggarwal*
Angew. Chem. Int. Ed., 2020, 59, 23107
Highlighted as Hot Paper

24. Formicamycin biosynthesis involves a unique reductive ring contraction
Zhiwei Qin, Rebecca Devine, Thomas J. Booth, Elliot H. E. Farrar, Matthew N. Grayson, Matthew I. Hutchings and Barrie Wilkinson
Chem. Sci., 2020, 11, 8125

23. Photocatalytic α‐Tertiary Amine Synthesis via C–H Alkylation of Unmasked Primary Amines
Alison S. H. Ryder, William B. Cunningham, George Ballantyne, Tom Mules, Anna G. Kinsella, Jacob Turner-Dore, Catherine M. Alder, Lee J. Edwards, Blandine S. J. McKay, Matthew N. Grayson and Alexander J. Cresswell
Angew. Chem. Int. Ed., 2020, 59, 14986

22. Enantioselective S‐H Insertion Reactions of α‐Carbonyl Sulfoxonium Ylides
Patrícia B. Momo, Alexandria N. Leveille, Elliot H. E. Farrar, Matthew N. Grayson, Anita E. Mattson and Antonio C. B. Burtoloso
Angew. Chem. Int. Ed., 2020, 59, 15554

21. Highly Sensitive Real-Time Isotopic Quantification of Water by ATR-FTIR
Cei B. Provis-Evans, Elliot H. E. Farrar, Matthew N. Grayson, Ruth L. Webster and Alfred Hill
Anal. Chem. 2020, 92, 7500

20. Functionalized Double Strain-Promoted Stapled Peptides for Inhibiting the p53-MDM2 Interaction 
Krishna Sharma, Alexander V. Strizhak, Elaine Fowler, Wenshu Xu, Ben Chappell, Hannah F. Sore, Warren R. J. D. Galloway, Matthew N. Grayson,* Yu Heng Lau,* Laura S. Itzhaki* and David R. Spring*
ACS Omega, 2020, 5, 1157

19. Density Functional Theory Transition-State Modeling for the Prediction of Ames Mutagenicity in 1,4 Michael Acceptors
Piers A. Townsend and Matthew N. Grayson*
J. Chem. Inf. Model., 2019, 59, 5099

18. Vinylidene Homologation of Boronic Esters and its Application to the Synthesis of the Proposed Structure of Machillene
James M. Fordham, Matthew N. Grayson* and Varinder K. Aggarwal*
Angew. Chem. Int. Ed., 2019, 58, 15268

17. Mechanistic Insights into a Chiral Phosphoric Acid-Catalyzed Asymmetric Pinacol Rearrangement
Bruno N. Falcone, Matthew N. Grayson* and Juan B. Rodriguez
J. Org. Chem. 2018, 83, 14683

16. Recent Developments and Applications of the Chiral Brønsted Acid Catalyzed Allylboration of Carbonyl Compounds
Daniel M. Sedgwick, Matthew N. Grayson, Santos Fustero and Pablo Barrio
Synthesis 2018, 50, 1935

15. Mechanism and Origins of Stereoselectivity in the Cinchona Thiourea- and Squaramide-Catalyzed Asymmetric Michael Addition of Nitroalkanes to Enones
Matthew N. Grayson*
J. Org. Chem. 2017, 82, 4396

Postdoctoral and PhD publications

14. Using Transition State Modelling to Predict Mutagenicity for Michael Acceptors
Timothy E. H. Allen,∥ Matthew N. Grayson,∥ Jonathan M. Goodman, Steve Gutsell and Paul J. Russell
∥ = Authors contributed equally
J. Chem. Inf. Model. 2018, 58, 1266

13. Chronology of CH···O Hydrogen Bonding from Molecular Dynamics Studies of the Phosphoric Acid-Catalyzed Allylboration of Benzaldehyde
Matthew N. Grayson,∥ Zhongyue Yang∥ and K. N. Houk
∥ = Authors contributed equally
J. Am. Chem. Soc. 2017, 139, 7717

12. Cinchona Urea-Catalyzed Asymmetric Sulfa-Michael Reactions: The Brønsted Acid− Hydrogen Bonding Model
Matthew N. Grayson and K. N. Houk
J. Am. Chem. Soc. 2016, 138, 9041

11. Chiral Brønsted Acid-Catalyzed Asymmetric Allyl (propargyl) boration Reaction of ortho-Alkynyl Benzaldehydes: Synthetic Applications and Factors Governing the Enantioselectivity
Elsa Rodríguez, Matthew N. Grayson, Amparo Asensio, Pablo Barrio, K. N. Houk and Santos Fustero
ACS Catal. 2016, 6, 2506

10. Theory and Modeling of Asymmetric Catalytic Reactions
Yu-hong Lam, Matthew N. Grayson, Mareike C. Holland, Adam Simon and K. N. Houk
Acc. Chem. Res. 2016, 49, 750

9. Cinchona alkaloid-catalyzed asymmetric conjugate additions: the bifunctional Brønsted acid–hydrogen bonding model
Matthew N. Grayson and K. N. Houk
J. Am. Chem. Soc. 2016, 138, 1170
Featured in Computational Organic Chemistry and Computational Chemistry Highlights

8. Efficient biosynthesis of fungal polyketides containing the dioxabicyclo-octane ring system
Xu-Ming Mao, Zha-Jun Zhan, Matthew N. Grayson, Man-Cheng Tang, Wei Xu, Yong-Quan Li, Wen-Bing Yin, Hsiao-Ching Lin, Yit-Heng Chooi, K. N. Houk and Yi Tang
J. Am. Chem. Soc. 2015, 137, 11904

7. Ruthenium-catalyzed asymmetric hydrohydroxyalkylation of butadiene: The role of the formyl hydrogen bond in stereochemical control
Matthew N. Grayson, Michael J. Krische and K. N. Houk
J. Am. Chem. Soc. 2015, 137, 8838
Featured in Organometallic Chemistry

6. Mechanistic insights into a BINOL-derived phosphoric acid-catalyzed asymmetric Pictet-Spengler reaction
Lois M. Overvoorde, Matthew N. Grayson, Yi Luo and Jonathan M. Goodman
J. Org. Chem. 2015, 80, 2634

5. Asymmetric Boronate Addition to o-Quinone Methides: Ligand Exchange, Solvent Effects, and Lewis Acid Catalysis
Matthew N. Grayson and Jonathan M. Goodman
J. Org. Chem. 2015, 80, 2056
Selected as a Featured Article

4. Base-Mediated Cascade Rearrangements of Aryl-Substituted Diallyl Ethers
Jolene P. Reid, Catherine A. McAdam, Adam J. S. Johnston, Matthew N. Grayson, Jonathan M. Goodman and Matthew J. Cook
J. Org. Chem. 2015, 80, 1472
Featured in Natural Product Man’s blog

3. Lewis Acid Catalysis and Ligand Exchange in the Asymmetric Binaphthol-Catalyzed Propargylation of Ketones
Matthew N. Grayson and Jonathan M. Goodman
J. Org. Chem. 2013, 78, 8796

2. Understanding the Mechanism of the Asymmetric Propargylation of Aldehydes Promoted by 1,1′-Bi-2-naphthol-Derived Catalysts
Matthew N. Grayson and Jonathan M. Goodman
J. Am. Chem. Soc. 2013, 135, 6142

1. Mechanistic Insights into the BINOL-Derived Phosphoric Acid-Catalyzed Asymmetric Allylboration of Aldehydes
Matthew N. Grayson, Silvina C. Pellegrinet and Jonathan M. Goodman
J. Am. Chem. Soc. 2012, 134, 2716