PhD in Asymmetric Synthesis and developing Lewis base-mediated transformations

About the Project

Our research is currently directed towards developing catalytic methods for the promotion of a range of synthetic transformations with varying applications in asymmetric synthesis. Current projects include the use of N-heterocyclic carbenes and isothioureas as enantioselective nucleophilic or Lewis-base catalysts and physical organic mechanistic studies designed toward understanding the mechanism of both N-heterocyclic carbene and isothiourea mediated transformations. The application of these methodologies to natural product synthesis is currently under development.

Funding is available to develop a range of novel enantioselective organocatalytic methods employing chiral Lewis-bases and other catalysts. The synthetic strategies that we develop will be used for the enantioselective synthesis of a range of carbo- and heterocyclic products, with mechanistic studies used to develop a comprehensive understanding of the reactions we study. Please see https://ads-group.squarespace.com/ for more information.

Students interested in undertaking a PhD in the Smith group in this research area should register their interest as soon as possible. Informal enquiries can be made to Prof Andrew Smith (ads10@st-andrews.ac.uk).

Please see: https://www.st-andrews.ac.uk/chemistry/prospective/pgr/ for the application procedure or e-mail chempg@st-andrews.ac.uk for more information regarding PhD opportunities at St Andrews. We encourage applications for the NextGenTech Centre for Doctoral training and from Chinese nationals through the St Andrews CSC Scheme (https://csc.wp.st-andrews.ac.uk/). There are opportunities for self-funded PhD students to make use of the St Andrews Handsel Scheme to fund the difference between home and international fees.

References

1. F. Zhao; C. Shu; C. M. Young; C. Carpenter-Warren; A. M. Z. Slawin, A. D. Smith; "Enantioselective Synthesis of α-Aryl-β2-Amino-esters via Cooperative Isothiourea and Brønsted Acid Catalysis" Angew. Chem. Int. Ed. 2021, 60, 11892-11900; https://doi.org/10.1002/anie.202016220
2. S. Qu, S.M. Smith, V. Laina-Martín, R. M. Neyyappadath, M. D. Greenhalgh and A. D. Smith, “Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters”, Angew. Chem. Int. Ed. 2020, 59, 16572-16578; https://doi.org/10.1002/anie.202004354
3. E. S. Munday, M. A. Grove, T. Feoktistova, A. C. Brueckner, D. M. Walden, C. M. Young, A. M. Z Slawin, A. D. Campbell, P. Ha-Yeon Cheong and A. D. Smith, “Isothiourea-Catalyzed Atropselective Acylation of Biaryl Phenols via Sequential Desymmetrization / Kinetic Resolution”, Angew. Chem. Int. Ed. 2020, 59, 7897-7905; https://doi.org/10.1002/anie.201916480
4. C. M. Young, A. Elmi, D. J. Pascoe, R. K. Morris, C. McLaughlin, A. M. Woods, A. B. Frost, A. de la Houpliere, K. B. Ling, T. K. Smith, A. M. Z. Slawin, P. H. Willoughby, S. L. Cockroft and A. D. Smith, “The Importance of 1,5-Oxygen•••Chalcogen Interactions in Enantioselective Isochalcogenourea Catalysis”, Angew. Chem. Int. Ed. 2020, 59, 3705-3710; DOI 10.1002/anie.201914421
5. C. McLaughlin, A. M. Z. Slawin and A. D. Smith, “Base-free Enantioselective C(1)-Ammonium Enolate Catalysis Exploiting Aryloxides: A Synthetic and Mechanistic Study”, Angew. Chem. Int. Ed. 2019, 58, 15111-15119; https://doi.org/10.1002/anie.201908627.