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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.
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). The group website can be accessed at https://ads-group.squarespace.com/
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 EaSiCAT Centre for Doctoral training (http://www.criticat.co.uk) 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.
[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.
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