The design, synthesis and application of (thio)urea-based organocatalysts for a range of C-C bond transformations
Citation:
Eimear Fleming, 'The design, synthesis and application of (thio)urea-based organocatalysts for a range of C-C bond transformations', [thesis], Trinity College (Dublin, Ireland). School of Chemistry, 2009, pp 276Download Item:
Abstract:
The identification and development of small chiral organic molecules capable of mimicking
the hydrogen-bonding capabilities of enzymes is the main thrust of this thesis concerning the
design and application of new (thio)urea containing catalysts for a variety of transformations.
Herein we detail the development of a new class of binaphthyl (thio)urea catalysts and the
evaluation of same in the asymmetric Friedel-Crafts reaction involving 7V-methyl indole and a
range of both activated and deactivated nitrostyrenes. A suite of materials of varying steric and
electronic characteristics were employed as catalysts in the enantioselective Friedel-Crafts
addition reaction. Whilst enantioselectivity of the Friedel-Crafts adducts was found to be
moderate (max. 50% ee), this was a significant improvement on the literature precedent,
highlighting the difficulty of such a transformation.
Author: Fleming, Eimear
Advisor:
Connon, StephenQualification name:
Doctor of Philosophy (Ph.D.)Publisher:
Trinity College (Dublin, Ireland). School of ChemistryNote:
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Chemistry, Ph.D., Ph.D. Trinity College Dublin.Metadata
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