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Advances in palladium catalysed Wacker-type oxidative transformations

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.

Identiferoai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:594448
Date January 2013
CreatorsLee, Darren S.
PublisherLoughborough University
Source SetsEthos UK
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
Sourcehttps://dspace.lboro.ac.uk/2134/13907

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