Chiral hypervalent iodine compounds are used as environmentally friendly, mild, and selective oxidants for many organic transformations. In this thesis, enantiomerically pure chiral hypervalent iodine reagents have been synthesized and used in the functionalization of different types of alkenes. A highly enantioselective oxyamination of alkenes with N-sulfonyl ureas employing chiral lactic acid-based hypervalent iodine reagents giving a facile synthesis of enantiomerically pure 2- arylproline derivatives is described. This is the first example of stereoselective oxyamination reactions under metal-free conditions. Then oxidative rearrangement of aryl-substituted ketones induced by lactate acid-based chiral hypervalent iodine reagents via 1,2 migration of the aryl moiety in the presence of alcohol nucleophiles is described leading to the �-arylated and �-oxygenated carbonyl compounds in enantiomerically pure form. This is the first stereoselective rearrangement reaction mediated by chiral hypervalent iodine reagents. Finally, all experimental details and characterization of the compounds are described.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:585302 |
| Date | January 2013 |
| Creators | Farid, Umar |
| Publisher | Cardiff University |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://orca.cf.ac.uk/53180/ |
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