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Lewis acid mediated reactions of silyl-substituted methylenecyclopropane and N-acyliminium ions

Lewis acid mediated reactions of silyl-substituted methylenecyclopropane and N-acyliminium ions
Lewis acid mediated reactions of silyl-substituted methylenecyclopropane and N-acyliminium ions
This thesis is concerned with Lewis acid mediated inter- and intramolecular reactions of silyl-substituted methylenecyclopropane with N-acyliminium ions, towards the formation of novel heterocyclic compounds.
Chapter 1 contains background information on synthetic organic chemistry relating to methylenecyclopropane, Lewis acids, N-acyliminium ions and related inter- and intramolecular reactions.
Chapter 2 describes the Lewis acid mediated intermolecular additions of silyl-substituted methylenecyclopropane to various substituted pyrrolidinone based N-acyliminium ions. The introduction, and subsequent removal, of an N-chiral group into the pyrrolidinone moiety is detailed. This N-chiral group has the effect of influencing the facial selectivity of the attack of the methylenecyclopropane and hence, the diastereoselectivity of the reaction.
Chapter 3 presents the attempts made to influence the reactivity of the silyl-substituted methylenecyclopropane towards electrophiles by constraining the silicon into a four or five membered ring. The synthesis of a novel silyl-substituted bismethylenecyclopropane compound is described.
Chapter 4 details the synthesis and intramolecular cyclisation studies of silyl-substituted pyrrolidinone precursors to generate novel heterocyclic compounds.
McDonald, Luke Eugene
a18b4404-4186-4133-a5d6-8948fd85400d
McDonald, Luke Eugene
a18b4404-4186-4133-a5d6-8948fd85400d
Kilburn, Jeremy
e5474f1d-b4b2-4d72-9712-7b1a6f340898

McDonald, Luke Eugene (2009) Lewis acid mediated reactions of silyl-substituted methylenecyclopropane and N-acyliminium ions. University of Southampton, School of Chemistry, Masters Thesis, 130pp.

Record type: Thesis (Masters)

Abstract

This thesis is concerned with Lewis acid mediated inter- and intramolecular reactions of silyl-substituted methylenecyclopropane with N-acyliminium ions, towards the formation of novel heterocyclic compounds.
Chapter 1 contains background information on synthetic organic chemistry relating to methylenecyclopropane, Lewis acids, N-acyliminium ions and related inter- and intramolecular reactions.
Chapter 2 describes the Lewis acid mediated intermolecular additions of silyl-substituted methylenecyclopropane to various substituted pyrrolidinone based N-acyliminium ions. The introduction, and subsequent removal, of an N-chiral group into the pyrrolidinone moiety is detailed. This N-chiral group has the effect of influencing the facial selectivity of the attack of the methylenecyclopropane and hence, the diastereoselectivity of the reaction.
Chapter 3 presents the attempts made to influence the reactivity of the silyl-substituted methylenecyclopropane towards electrophiles by constraining the silicon into a four or five membered ring. The synthesis of a novel silyl-substituted bismethylenecyclopropane compound is described.
Chapter 4 details the synthesis and intramolecular cyclisation studies of silyl-substituted pyrrolidinone precursors to generate novel heterocyclic compounds.

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Published date: 11 May 2009
Organisations: University of Southampton

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Local EPrints ID: 72953
URI: http://eprints.soton.ac.uk/id/eprint/72953
PURE UUID: c7960bff-8430-4350-a2ba-5c5e4622ecc7

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Date deposited: 01 Mar 2010
Last modified: 29 Jan 2020 13:12

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