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Novel methods for the synthesis of small ring systems

Pugh, David (2011) Novel methods for the synthesis of small ring systems. PhD thesis, University of York.

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Abstract

Chapter 1 briefly reviews telescoped reactions, in particular tandem oxidation processes, detailing the background to the development of the methodology presented here, and sets out the aims for the Thesis. Chapter 2 reviews cyclopropanation methods and examines the preparation and use of triisopropylsulfoxonium tetrafluoroborate II for the preparation of gemdimethylcyclopropanes for a range of α,β-unsaturated compounds including ketones, esters, amides, nitriles and nitro-compounds (Scheme I). Chapter 2 also examines potential applications for the methodology, outlining a route towards the synthesis of chrysanthemic acid as well as attempts towards rearrangement methodology. Chapter 3 demonstrates the preparation of 3-substituted oxindoles from substituted anilides in a copper-mediated cyclisation-decarboxylation sequence (Scheme II). This sequence is demonstrated for a range of alkyl, aryl and heteroaryl substituents in the 3-position, with methyl, benzyl and PMB protection on the nitrogen atom. Further development of the copper-cyclisation methodology leading to a catalytic system is presented, along with initial work towards a decarboxylative allylation of oxindoles.

Item Type: Thesis (PhD)
Academic Units: The University of York > Chemistry (York)
Depositing User: Mr David Pugh
Date Deposited: 13 Dec 2011 12:42
Last Modified: 08 Aug 2013 08:47
URI: http://etheses.whiterose.ac.uk/id/eprint/1959

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