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Investigation of Aminonitriles as Organocatalysts.

Vagkidis, Nikolaos (2019) Investigation of Aminonitriles as Organocatalysts. MSc by research thesis, University of York.

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Abstract

This project built upon previous work with amino acid derivatives in the Clarke group. Originally, L-valine nitrile 4 and L-proline nitrile 5 were investigated for the first time as catalysts for the aldol reaction of 4-nitrobenzaldehyde 1 and cyclohexanone 2 in an array of organic solvents. Interestingly, a new proline derivative 6 was synthesised and also investigated for the first time. Aminonitrile 4 afforded the aldol adducts with an interesting major syn diastereomer but the results in terms of conversion and enantioselectivity were discouraging. Aminonitrile 5 showed a better catalytic efficiency than 4 in terms of conversion, however, the enantioselectivity was moderate. Proline imidate 6 was investigated as an organocatalyst for the first time and promising results were gained. L-Proline imidate 6 was trialled in an array of organic solvents and different aldehydes and 6 afforded the anti (major) aldol diastereomer in a good enantiomeric excess with up to 94% ee.

Item Type: Thesis (MSc by research)
Academic Units: The University of York > Chemistry (York)
Depositing User: Mr Nikolaos Vagkidis
Date Deposited: 30 Apr 2019 13:59
Last Modified: 30 Apr 2019 13:59
URI: http://etheses.whiterose.ac.uk/id/eprint/23730

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