C2-symmetric amino acid amide-derived organocatalysts
C2-symmetric amino acid amide-derived organocatalysts
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.
aldol reactions, amino acids, Michael additions, organocatalysis
567-586
Al-Taie, Zahraa S.
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Coles, Simon J.
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Congreve, Aileen
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Ford, Dylan
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Green, Lucy
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Horton, Peter N.
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Jones, Leigh F.
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Kett, Pippa
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Kraehenbuehl, Rolf
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Murphy, Patrick J.
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Tizzard, Graham J.
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Willmore, Niles B.
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Wright, Oliver T.
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24 August 2024
Al-Taie, Zahraa S.
07181947-5786-4d1e-ac8e-7a532d692934
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Congreve, Aileen
bc76e29e-e9da-496a-bec1-dbab7765fb8c
Ford, Dylan
40ed3d8d-9a35-4f16-94d9-e1b88e91bd42
Green, Lucy
c348a944-343d-4a76-aefe-0c6b30dc4a5b
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Jones, Leigh F.
fdb8562f-36c2-4f8f-9221-947e1d05a45e
Kett, Pippa
6ce71493-fd2e-417c-8114-d0c0ed42084c
Kraehenbuehl, Rolf
66d9e8a7-ad86-4680-ae98-e6d7e4c479ed
Murphy, Patrick J.
5ab567ae-c42c-44d4-8ae4-8b376cf2e6e6
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Willmore, Niles B.
1c893f50-fe20-415b-aa05-a25c22ce02b4
Wright, Oliver T.
f487db92-c5d3-46f2-8ff1-50ab833e69e0
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), .
(doi:10.3390/reactions5030027).
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.
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reactions-05-00027
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Accepted/In Press date: 16 August 2024
Published date: 24 August 2024
Keywords:
aldol reactions, amino acids, Michael additions, organocatalysis
Identifiers
Local EPrints ID: 495355
URI: http://eprints.soton.ac.uk/id/eprint/495355
PURE UUID: 3d674ffa-142d-4616-8a33-8e8c6699b9c6
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Date deposited: 11 Nov 2024 18:13
Last modified: 12 Nov 2024 02:39
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Contributors
Author:
Zahraa S. Al-Taie
Author:
Aileen Congreve
Author:
Dylan Ford
Author:
Lucy Green
Author:
Peter N. Horton
Author:
Leigh F. Jones
Author:
Pippa Kett
Author:
Rolf Kraehenbuehl
Author:
Patrick J. Murphy
Author:
Niles B. Willmore
Author:
Oliver T. Wright
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