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C2-Symmetric Amino Acid Amide-Derived Organocatalysts

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C2-Symmetric Amino Acid Amide-Derived Organocatalysts. / Al-Taie, Zahraa; Coles, S.J.; Horton, Peter et al.
In: Reactions, Vol. 5, No. 3, 24.08.2024, p. 567-586.

Research output: Contribution to journal › Article › peer-review

HarvardHarvard

Al-Taie, Z, Coles, SJ, Horton, P, Kraehenbuehl, R, Murphy, P & Tizzard, G 2024, 'C2-Symmetric Amino Acid Amide-Derived Organocatalysts', Reactions, vol. 5, no. 3, pp. 567-586. <https://doi.org/10.3390/reactions5030027>

APA

Al-Taie, Z., Coles, S. J., Horton, P., Kraehenbuehl, R., Murphy, P., & Tizzard, G. (2024). C2-Symmetric Amino Acid Amide-Derived Organocatalysts. Reactions, 5(3), 567-586. https://doi.org/10.3390/reactions5030027

CBE

Al-Taie Z, Coles SJ, Horton P, Kraehenbuehl R, Murphy P, Tizzard G. 2024. C2-Symmetric Amino Acid Amide-Derived Organocatalysts. Reactions. 5(3):567-586.

MLA

Al-Taie, Zahraa et al. "C2-Symmetric Amino Acid Amide-Derived Organocatalysts". Reactions. 2024, 5(3). 567-586.

VancouverVancouver

Al-Taie Z, Coles SJ, Horton P, Kraehenbuehl R, Murphy P, Tizzard G. C2-Symmetric Amino Acid Amide-Derived Organocatalysts. Reactions. 2024 Aug 24;5(3):567-586.

Author

Al-Taie, Zahraa ; Coles, S.J. ; Horton, Peter et al. / C2-Symmetric Amino Acid Amide-Derived Organocatalysts. In: Reactions. 2024 ; Vol. 5, No. 3. pp. 567-586.

RIS

TY - JOUR

T1 - C2-Symmetric Amino Acid Amide-Derived Organocatalysts

AU - Al-Taie, Zahraa

AU - Coles, S.J.

AU - Horton, Peter

AU - Kraehenbuehl, Rolf

AU - Murphy, Paddy

AU - Tizzard, Graham

PY - 2024/8/24

Y1 - 2024/8/24

N2 - 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.

AB - 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.

M3 - Article

VL - 5

SP - 567

EP - 586

JO - Reactions

JF - Reactions

SN - 2624-781X

IS - 3

ER -