C 2 -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.; Wright, Oliver T.

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.

Citation

Al-Taie, Z. S., Coles, S. J., Congreve, A., Ford, D., Green, L., Horton, P. N., Jones, L. F., Kett, P., Kraehenbuehl, R., Murphy, P. J., Tizzard, G. J., Willmore, N. B., & Wright, O. T. (2024). C 2 -Symmetric Amino Acid Amide-Derived Organocatalysts. Reactions, 5(3), 567-586. https://doi.org/10.3390/reactions5030027

• Journal Article Type: Article
• Acceptance Date: Aug 16, 2024
• Online Publication Date: Aug 24, 2024
• Publication Date: 2024-09
• Deposit Date: Sep 13, 2024
• Publicly Available Date: Sep 13, 2024
• Journal: Reactions
• Electronic ISSN: 2624-781X
• Publisher: MDPI
• Peer Reviewed: Peer Reviewed
• Volume: 5
• Issue: 3
• Pages: 567-586
• DOI: https://doi.org/10.3390/reactions5030027
• Keywords: amino acids, organocatalysis, Michael additions, aldol reactions
• Public URL: https://durham-repository.worktribe.com/output/2820464