Thesis-2005-HorroPita.pdf (4.65 MB)
The development and application of the anionic amino-Cope rearrangement
thesis
posted on 2018-06-28, 11:16 authored by Catarina Horro PitaThe anionic amino-Cope rearrangement is currently being developed by our group as a
new synthetic protocol. Our ultimate goal is the one-pot asymmetric synthesis of
compounds such as (A), with up to 3 contiguous chiral centres, via an amino-Cope
rearrangement and subsequent enamine derivatisation and hydrolysis.
[Illustration omitted.]
The mechanism of the anionic amino-Cope rearrangement is still a matter of debate and
we have investigated the effect of solvent and substituents on the enantioselectivity
observed in the reaction. The aim of this study was to find the optimal conditions for the
anionic amino-Cope rearrangement, eliminating—or at least minimising—competing
reaction pathways that can reduce the enantioselectivity of the process.
In addition, the aldehyde product of the amino-Cope rearrangement has been used as a
chiral building block for the synthesis of heterocycles such as tetrahydropyrans (B) and
lactones (D). The synthesis of piperidines (C) has now been achieved, enhancing the
scope of this rearrangement.
[Illustration omitted.]
Funding
Loughborough University, Department of Chemistry. Syngenta AG.
History
School
- Science
Department
- Chemistry
Publisher
© Catarina Horro PitaPublisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Publication date
2005Notes
A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.Language
- en