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Advances in palladium catalysed wacker-type oxidative transformations

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posted on 06.01.2014 by Darren S. Lee
The development and optimisation of conditions for oxidative Wacker-type cyclisations followed by establishing the reaction scope are reported. Building upon the achievements in the field of oxidative Wacker-type reactions that has recently gathered interest, hydroxylamines and hydrazines were converted to isoxazolidines and pyrazolidines respectively. Secondary hydroxylamines cyclised yielding syn-isoxazolidines with excellent diastereoselectivities, whereas secondary hydrazines cyclised yielding anti-pyrazolidines but still maintained a high level of diastereoselectivity. Additionally, an enantioselective variant was explored. Isoxazolidines were successfully transformed to the corresponding 1,3-amino alcohols, which were further converted to amino sugar derivatives.

Funding

Loughborough University

History

School

  • Science

Department

  • Chemistry

Publisher

© Darren Lee

Publication date

2013

Notes

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

EThOS Persistent ID

uk.bl.ethos.594448

Language

en

Exports