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.
Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:594448 |
Date | January 2013 |
Creators | Lee, Darren S. |
Publisher | Loughborough University |
Source Sets | Ethos UK |
Detected Language | English |
Type | Electronic Thesis or Dissertation |
Source | https://dspace.lboro.ac.uk/2134/13907 |
Page generated in 0.0009 seconds