Use this URL to cite or link to this record in EThOS: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.535992
Title: Amine-promoted alkene aziridination
Author: Pullin, Robert David Charles
Awarding Body: Imperial College London
Current Institution: Imperial College London
Date of Award: 2011
Availability of Full Text:
Access through EThOS:
Full text unavailable from EThOS. Please try the link below.
Access through Institution:
Abstract:
Aziridines, the smallest saturated aza-heterocycle, are not only prevalent in several natural products, but also represent a versatile synthetic tool for the chemist via exploitation of the strained ring system. Research described in this thesis concerns the chemistry of N-N ylides (aminimines), which were utilised in a novel tertiary amine-promoted organocatalytic approach to the aziridination of α,β-unsaturated carbonyl compounds. Through the use of modified conditions two important classes of substrates, dienones and alpha-enolizable enones, both of which had previously shown poor reactivity with the system, can now be aziridinated in good yields. Studies have also focused on the development of an asymmetric variant of the methodology using chiral tertiary amine promoters. A variety of novel chiral six-membered 1,4-heterocycles and cinchona alkaloid derivatives have been synthesised and their utility towards asymmetric alkene aziridination has been assessed, aiding the understanding of the proposed transition state model for the reaction.
Supervisor: Armstrong, Alan Sponsor: EPSRC ; Syngenta
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.535992  DOI: Not available
Share: