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1
Towards the total synthesis of keramaphidin B
Published 2016“…The enantio- and diastereoselective Michael addition of a δ-valerolactone-derived pronucleophile to a substituted furanyl nitroolefin catalysed by a bifunctional cinchonine-derived thiourea has been used as the key stereocontrolling step in a new synthetic strategy to the heavily functionalised piperidine core of keramaphidin B.…”
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2
Immobilisation and application of bifunctional iminophosphorane organocatalysts
Published 2014“…<p>Bifunctional iminophosphoranes, containing a triaryl-substituted iminophosphorane and bis(3,5- trifluoromethyl)phenyl thiourea on a single enantiomer scaffold are novel asymmetric superbase organocatalysts reported by the Dixon group in 2014. …”
Thesis -
3
Enantioselective organocatalytic Michael addition of malonate esters to nitro olefins using bifunctional cinchonine derivatives.
Published 2005“…A family of 9-amino(9-deoxy) epicinchonine derivatives, possessing a range of mono- and bidentate hydrogen bond donor groups at the 9-position, were synthesised and evaluated for asymmetric organocatalytic activity in the dimethyl malonate Michael addition to beta-nitrostyrene; thiourea derivative was identified as the most effective bifunctional organic catalyst and found to induce high enantioselectivity in the malonate ester Michael addition reaction to a range of nitro olefins.…”
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4
Enantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters
Published 2016“…The low acidity of the alkyl thiol pro-nucleophiles is overcome by the high Brønsted basicity of the catalyst and the chiral scaffold/thiourea hydrogen-bond donor moiety provides the required enantiofacial discrimination in the addition step. …”
Journal article -
5
Catalytic enantioselective methods for challenging polar addition reactions
Published 2021“…The ability of a BIMP catalyst to activate high-pKa aryl methyl ketone pro-nucleophiles is emphasised against the backdrop of traditional Cinchona and thiourea organocatalysis. The broad downstream utility of the β-hydroxy ketone products is demonstrated, along with an efficient scale-up protocol showcasing catalyst recyclability. …”
Thesis -
6
Development and application of a new class of potent bifunctional organocatalysts
Published 2015“…The reaction required the development of BIMP catalysts such as <b>4</b> that incorporated an amide thiourea H-bond donor group. 31 examples were investigated with quantitative yields and up to 96% ee obtained in the formation of β-mercaptoesters <b>7</b>. …”
Thesis