Controlled Access. Restriction lift date: 2033-09-30
Synthesis of chiral cycloperoxides
Loading...
Files
Date
2023
Authors
Gandhi, Hirenkumar
Journal Title
Journal ISSN
Volume Title
Publisher
University College Cork
Published Version
Abstract
Chapter One is a literature review of different synthetic approaches to acyclic peroxides. This review covers various methods including metal-catalysed peroxidations, organocatalysed reactions, singlet oxygen or ozone-mediated reactions, and finally miscellaneous methods.
Chapter Two describes the project background, and the significance of biologically active chiral cycloperoxides. Previous work on the asymmetric peroxidation of unsaturated aldehydes, as well as our subsequent investigation of the scope of this chemistry, is included. Methods for determining the enantioselectivity of these transformations are also described.
In Chapter Three, the synthesis of a variety of novel quinine analogues as potential peroxidation catalysts is outlined. Additionally, the ability of these quinine derivatives to act as anti-parasitic agent against T. cruzi, the causative agent in Chagas disease, is examined.
Chapter Four describes the development of routes to chiral cycloperoxides based on our optimised asymmetric peroxidation chemistry. This chapter focuses on the synthesis of both mono- and disubstituted 1,2-dioxolanes. During the course of this work, a novel methodology for preparing γ,δ-unsaturated-β-keto esters was also discovered and optimised.
In Chapter Five, the organocatalysed peroxidation of γ,δ-unsaturated-β-ketoesters is examined. This chemistry opens up access to 3,5-disubstituted 1,2-dioxolanes via a silvermediated cyclisation step.
Asymmetric peroxidation using hydrogen peroxide is discussed in Chapter Six. This chapter also describes how this chemistry can be applied to the synthesis of 1,2-dioxanes which are structurally similar to the potent anti-malarial compounds Yingzhaosu A and C.
Conclusions and future directions are detailed in Chapter 7.
Finally, full experimental procedures, including spectroscopic and analyticsal data, are provided in Chapter 8.
Description
Controlled Access
Keywords
Cycloperoxides
Citation
Gandhi, H. 2023. Synthesis of chiral cycloperoxides. PhD Thesis, University College Cork.