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Dr Matthew N. Grayson

List of Publications 
Google Scholar Profile

Matthew Grayson is a Girton College Tucker-Price Research Fellow in Organic Chemistry at the University of Cambridge.

After graduating with 1st Class Honours in Natural Sciences at the University of Cambridge, Matt obtained his PhD at Cambridge in 2014 with Jonathan M. Goodman working on understanding and developing asymmetric methodology in organic chemistry. In 2014, he took up an independent Girton College Research Fellowship at Cambridge. As a recipient of a Lindemann Trust Fellowship, Matt conducted postdoctoral research in the group of K. N. Houk at the University of California, Los Angeles during the full calendar year of 2015 before returning to Cambridge to continue his fellowship.

Research Interests

The synthesis of enantiopure molecules is of fundamental importance in the preparation of fragrances, flavours, materials, catalysts, agricultural chemicals and pharmaceutical drugs. However, the discovery of new asymmetric reactions needed to synthesise these chiral molecules is still heavily reliant upon trial-and-error.

Matt’s research focuses on discovering the mechanisms of organic and enzymatic reactions using computational methods. These results are then applied to the rational design of new reactions and catalysts.

Current research areas and selected publications:

  • Organocatalysis (J. Am. Chem. Soc.2016138, 9041.; J. Am. Chem. Soc.2016138, 1170.; J. Am. Chem. Soc. 2013135, 6142.; J. Am. Chem. Soc. 2012134, 2716.)
  • Organometallics (J. Am. Chem. Soc. 2015137, 8838.)
  • Biosynthesis (J. Am. Chem. Soc. 2015137, 11904.)
  • Reaction Dynamics
  • Toxicology

Publications

  1. Chronology of CH···O Hydrogen Bonding from Molecular Dynamics Studies of the Phosphoric Acid-Catalyzed Allylboration of Benzaldehyde
    Grayson, M. N.*; Yang, Z.*; Houk, K. N.
    *=Authors contributed equally
    J. Am. Chem. Soc. 2017, Just Accepted Manuscript.
    DOI: 10.1021/jacs.7b03847

  2. Mechanism and Origins of Stereoselectivity in the Cinchona Thiourea- and Squaramide-Catalyzed Asymmetric Michael Addition of Nitroalkanes to Enones
    Grayson, M. N.
    J. Org. Chem. 201782, 4396.
    DOI: 10.1021/acs.joc.7b00521

  3. Cinchona Urea-Catalyzed Asymmetric Sulfa-Michael Reactions: The Brønsted Acid-Hydrogen Bonding Model
    Grayson, M. N.; Houk, K. N.
    J. Am. Chem. Soc.2016, 138, 9041.
    DOI: 10.1021/jacs.6b05074

  4. Chiral Brønsted Acid-Catalyzed Asymmetric Allyl(propargyl)boration Reaction of ortho-Alkynyl Benzaldehydes: Synthetic Applications and Factors Governing the Enantioselectivity
    Rodriguez, E.; Grayson, M. N.; Asensio, A.; Barrio, P.; Houk, K. N.; Fustero, S.
    ACS Catal.2016, 6, 2506.
    DOI: 10.1021/acscatal.6b00209

  5. Theory and Modeling of Asymmetric Catalytic Reactions
    Lam, Y.-h.; Grayson, M. N.; Holland, M. C.; Simon, A.; Houk, K. N.
    Acc. Chem. Res.2016, 49, 750.
    DOI: 10.1021/acs.accounts.6b00006

  6. Cinchona Alkaloid-Catalyzed Asymmetric Conjugate Additions: The Bifunctional Brønsted Acid–Hydrogen Bonding Model
    Grayson, M. N.; Houk, K. N.
    J. Am. Chem. Soc.2016138, 1170.
    DOI: 10.1021/jacs.5b13275
    This paper was featured in:
    Computational Organic Chemistry
    Computational Chemistry Highlights

  7. Efficient Biosynthesis of Fungal Polyketides Containing the Dioxabicyclo-octane Ring System
    Mao, X.-M.; Zhan, Z.-J.; Grayson, M. N.; Tang, M.-C.; Xu, W.; Li, Y.-Q.; Yin, W.-B.; Lin, H.-C.; Chooi, Y.-H.; Houk, K. N.; Tang, Y.
    J. Am. Chem. Soc. 2015137, 11904.
    DOI: 10.1021/jacs.5b07816

  8. Ruthenium-Catalyzed Asymmetric Hydrohydroxyalkylation of Butadiene: The Role of the Formyl Hydrogen Bond in Stereochemical Control
    Grayson, M. N.; Krische, M. J.; Houk, K. N.
    J. Am. Chem. Soc. 2015137, 8838.
    DOI: 10.1021/jacs.5b04844
    This paper was featured in:
    Organometallic Chemistry

  9. Mechanistic insights into a BINOL-derived phosphoric acid-catalyzed asymmetric Pictet-Spengler reaction
    Overvoorde, L. M.; Grayson, M. N.; Luo, Y.; Goodman, J. M.
    J. Org. Chem. 201580, 2634.
    DOI: 10.1021/jo5028134

  10. Asymmetric Boronate Addition to o-Quinone Methides: Ligand Exchange, Solvent Effects and Lewis Acid Catalysis
    Grayson, M. N.; Goodman, J. M.
    J. Org. Chem. 201580, 2056.
    DOI: 10.1021/jo502616a
    Selected as a Feature Article

  11. Base Mediated Cascade Rearrangements of Aryl Substituted Diallyl Ethers
    Reid, J. P.; McAdam, C. A.; Johnston, A. J. S.; Grayson, M. N.; Goodman, J. M.; Cook, M. J.
    J. Org. Chem. 201580, 1472.
    DOI: 10.1021/jo502403n
    This paper was featured in:
    Organic Chemistry Portal

  12. Lewis Acid Catalysis and Ligand Exchange in the Asymmetric Binaphthol-Catalyzed Propargylation of Ketones
    Grayson, M. N.; Goodman, J. M.
    J. Org. Chem. 201378, 8796.
    DOI: 10.1021/jo401611q

  13. Understanding the Mechanism of the Asymmetric Propargylation of Aldehydes Promoted by 1,1′-Bi-2-naphthol-Derived Catalysts
    Grayson, M. N.; Goodman, J. M.
    J. Am. Chem. Soc. 2013135, 6142.
    DOI: 10.1021/ja3122137

  14. Mechanistic Insights into the BINOL-Derived Phosphoric Acid-Catalyzed Asymmetric Allylboration of Aldehydes
    Grayson, M. N.; Pellegrinet, S. C.; Goodman, J. M.
    J. Am. Chem. Soc. 2012134, 2716.
    DOI: 10.1021/ja210200d     
    This paper was featured in:  
    JACS Image Challenge

 

Telephone number

01223 763854