Thesis
Design, synthesis and exploration of P-chiral phosphoramidites: Implementations in asymmetric conjugate additions to cycloalkenyl ketones
- Abstract:
- This thesis explores the development and application of stereoselective and diastereoselective methodologies for synthesizing complex chiral molecules using asymmetric catalysis. Chapter 1 introduces the importance of chirality in organic synthesis, highlighting key strategies for achieving enantiomerically enriched compounds and the design principles of privileged ligands in asymmetric catalysis. Chapter 2 focuses on asymmetric conjugate additions (ACAs) to cycloalkenyl ketones, detailing the discovery, optimization, and scope of a copper-catalyzed ACA reaction utilizing alkylzirconocene nucleophiles. This methodology offers a stereodivergent approach to access 1,2-disubstituted cyclic frameworks with high enantioselectivities. Chapter 3 investigates the ligand space of P-stereogenic phosphoramidites, exploring modifications to the BINOL backbone and amine substituents to enhance the diastereoselectivity and performance of ligands in the ACA of challenging substrates. Finally, Chapter 4 develops novel diastereoselective strategies for synthesizing the Pstereogenic phosphoramidite ligand L22S, crucial for achieving high enantioselectivities in exocyclic ACA systems. Discussion of both the challenges encountered and the promising outcomes is included.
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(Preview, Dissemination version, pdf, 7.1MB, Terms of use)
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Authors
Contributors
+ Fletcher, S
- Institution:
- University of Oxford
- Division:
- MPLS
- Department:
- Chemistry
- Sub department:
- Organic Chemistry
- Role:
- Supervisor
+ Sidera Portela, M
- Role:
- Supervisor
+ University of Oxford
More from this funder
- Funder identifier:
- https://ror.org/052gg0110
- Programme:
- I am pleased to inform you that the Department of Chemistry is able to offer you a fully-funded graduate studentship towards your DPhil in Organic Chemistry to work with Professor Stephen Fletcher. It will cover your course fees and provide a stipend at a UK Research Council rate (£15,285 for 2020/21 academic year) for 3 years. You will be paid 50% from the EPSRC Doctoral Training Partnership account (DTP) and 50% from Departmental Funds.
+ Engineering and Physical Sciences Research Council
More from this funder
- Funder identifier:
- https://ror.org/0439y7842
- Programme:
- I am pleased to inform you that the Department of Chemistry is able to offer you a fully-funded graduate studentship towards your DPhil in Organic Chemistry to work with Professor Stephen Fletcher. It will cover your course fees and provide a stipend at a UK Research Council rate (£15,285 for 2020/21 academic year) for 3 years. You will be paid 50% from the EPSRC Doctoral Training Partnership account (DTP) and 50% from Departmental Funds.
- DOI:
- Type of award:
- DPhil
- Level of award:
- Doctoral
- Awarding institution:
- University of Oxford
- Language:
-
English
- Keywords:
- Subjects:
- Deposit date:
-
2026-04-27
- ARK identifier:
Terms of use
- Copyright holder:
- Martín Fernández Pascual
- Copyright date:
- 2025
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