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Thesis-2005-HorroPita.pdf (4.65 MB)

The development and application of the anionic amino-Cope rearrangement

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posted on 2018-06-28, 11:16 authored by Catarina Horro Pita
The 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 Pita

Publisher 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

2005

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.

Language

  • en

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