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The Selective Dehydration of Sugars in the Sustainable Synthesis of Chiral Fragments and Fluoroalkane Generation from Prochiral Substrates

Szpara, Rachel; (2022) The Selective Dehydration of Sugars in the Sustainable Synthesis of Chiral Fragments and Fluoroalkane Generation from Prochiral Substrates. Doctoral thesis (Ph.D), UCL (University College London). Green open access

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Abstract

Waste biomass is abundant in sugars (both hexoses and pentoses), making them a renewable source of chiral building blocks which may be utilised in synthetic chemistry. Although large percentages of waste biomass are useful (~17% sugar by weight), large-scale production of drug precursors and THF-containing molecules often utilise alternative synthetic routes. Trapping of sugars in their open-chain form allows them to be treated as chiral polyol reagents for attaching chiral centres. A variety of different sugar thioacetals may be selectively dehydrated to produce the corresponding ketene thioacetals under mild basic conditions. The reactivity of the resulting ketene thioacetals has been explored, with cyclisation induced to produce a range of novel heterocycles. Further selective dehydration has been carried out in some cases. Insight into the mechanism of dehydration has been provided, with studies into the intermediate structures. With the demand for chiral heterocyclic rings increasing in pharmaceuticals, we present sustainable methods for the synthesis of useful compounds from innately chiral fragments. In addition, studies into the formation of chiral fluorine compounds have been explored, with the application of ene-reductase biocatalysis in an effort for a more sustainable approach to synthetic chiral fluorine generation.

Type: Thesis (Doctoral)
Qualification: Ph.D
Title: The Selective Dehydration of Sugars in the Sustainable Synthesis of Chiral Fragments and Fluoroalkane Generation from Prochiral Substrates
Open access status: An open access version is available from UCL Discovery
Language: English
Additional information: Copyright © The Author 2022. Original content in this thesis is licensed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY-NC 4.0) Licence (https://creativecommons.org/licenses/by-nc/4.0/). Any third-party copyright material present remains the property of its respective owner(s) and is licensed under its existing terms. Access may initially be restricted at the author’s request.
UCL classification: UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL
URI: https://discovery.ucl.ac.uk/id/eprint/10153870
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