C2-Symmetric Amino Acid Amide-Derived Organocatalysts

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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.
Original languageEnglish
Pages (from-to)567-586
JournalReactions
Volume5
Issue number3
Publication statusPublished - 24 Aug 2024
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