New axially chiral amine organocatalysts

Strutt, Ian (2014) New axially chiral amine organocatalysts. Doctoral thesis, University of East Anglia.

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Abstract

Organocatalysis has become one of the most popular areas of research within
organic chemistry over the past 15 years. This is due to the fact that, usually under
mild conditions, it is possible to access either highly functionalized or previously
inaccessible structural motifs using this relatively new type of catalysis.
Firstly, methodology is reported for the synthesis and use of tertiary amine
organocatalysts based on the now ubiquitous binaphthyl backbone. The tertiary
amines synthesized were shown to be effective nitrogen transfer reagents in the
asymmetric aziridination of chalcone substrates, with enantiomeric excesses of up to
37% seen. The first example of an isolated chiral hydrazinium salt being used as a
nitrogen transfer reagent for the aziridination of enones is also described.
Secondly, a range of α-substituted secondary amines based on the binaphthyl
backbone has been synthesized from easily accessible iminium salts. Preliminary
catalyst testing showed them to be interesting alternatives to the more commonly
seen proline-derived catalysts for asymmetric conjugate additions reactions between
cyclic enones and malonates, with enantiomeric excesses of 24% seen using
optimized conditions.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Mia Reeves
Date Deposited: 30 Jun 2015 14:14
Last Modified: 30 Jun 2015 14:14
URI: https://ueaeprints.uea.ac.uk/id/eprint/53435
DOI:

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