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H2020Individual fellowship2016–2018

CombiCat · Combined Catalysis: Enhancing Asymmetric Synthesis

Horizon 2020 — Marie Skłodowska-Curie Actions

Duration
2016-10-01 → 2018-09-30
EU contribution
€183,455
Participants
1
Scheme
MSCA-IF-EF-ST

Lines connect the coordinator with its partners.

Results in brief

Combined Catalysis: Enhancing Asymmetric Synthesis

This project addressed the synthesis of small organic molecules using two catalyst approaches. The particular topic examined was the cyclisation of acyclic compounds to nitrogen-containing rings, via a process called 'cycloisomerization'. Progress was made in studying asymmetric cycloisomerizations, where one enantiomer (mirror image form) of a molecule is prepared. The ability of a catalyst to control this reaction, rather than the substrate itself, is important as this allows chemists to control the reaction outcome. This project aimed to explore the use of two catalysts to improve control over such processes. This work is important for society as the synthesis of new drug molecules requires efficient chemical processes, which generate minimal waste, and allow high control over the target molecule. Cycloisomerization fulfils these aims, and this project aimed to advance the state of the art in this area. The objectives of the work were: 1. To establish robust methods for synthesis of substrates from cheap/commercial materials 2. To explore substrate scope and double stereodifferentiation in cyclisation reactions 3. To explore one-pot multicatalytic processes using combinations of transition metal and organocatalysis 4. Development of processes in which single enantiomer substrates are reacted using two chiral catalysts, and extension of this to diastereodivergent kinetic resolutions.

Data: CORDIS, © European Union

Project objective

The stereoselective synthesis of small organic molecules depends on robust catalytic methods. Despite many advances in enantioselective synthesis, an unsolved challenge in catalysis is the translation of enantioselective catalytic reactions to diastereoselective reactions – where a chiral catalyst controls the outcome of reaction of a chiral substrate. In this proposal, we seek to investigate this 'double stereodifferentiation' in various organocatalytic reactions, and in transition metal-catalyzed cycloisomerization, two fields which take advantage of the expertise of the host group and the experienced researcher. We further aim to explore the union of these two fields using 'Combined catalysis' – specifically, in dual catalytic processes through which we seek to improve stereoselective syntheses of small organic molecules attractive to the pharmaceutical industry. The culmination of the project will be cascade dual catalytic processes, where the organocatalyst serves to activate the substrate towards metal-catalyzed cycloisomerization, and also to mediate a further asymmetric synthetic transformation.The successful completion of these goals will require the combined expertise of the two project partners: in metal catalysis (the host group) and organocatalysis (the ER), with the proposal being based on preliminary results in both areas.

Original text from CORDIS.

Participants

  • THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD · OxfordCoordinatorUnited Kingdom

Links

Data: CORDIS, © European Union