C2-Symmetric amino acid amide-derived organocatalysts

Al-Taie, Zahraa S., Coles, Simon J., Congreve, Aileen, Ford, Dylan, Green, Lucy, Horton, Peter N., Jones, Leigh F., Kett, Pippa, Kraehenbuehl, Rolf, Murphy, Patrick J., Tizzard, Graham J., Willmore, Niles B. and Wright, Oliver T. 2024. C2-Symmetric amino acid amide-derived organocatalysts. Reactions 5 (3) , pp. 567-586. 10.3390/reactions5030027

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Abstract

N-alkylated C2-symmetric amino acid amide derivatives were shown to catalyse the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 44%. The corresponding trifluoroacetic acid salts also catalysed the aldol reaction between 4-nitrobenzaldehyde and hydroxyacetone, leading to the formation of predominantly syn-aldol products in up to 55% ee. Aspects of the solvent dependence of the aldol reaction and the H-bonding of the catalyst were investigated.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Chemistry
Publisher:	MDPI
ISSN:	2624-781X
Date of First Compliant Deposit:	29 August 2024
Date of Acceptance:	16 August 2024
Last Modified:	29 Aug 2024 09:15
URI:	https://orca.cardiff.ac.uk/id/eprint/171629

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