C 2 -Symmetric Amino Acid Amide-Derived Organocatalysts †

Zahraa S. Al-Taie; Simon J. Coles; Aileen Congreve; Dylan Ford; Lucy Green; Peter N. Horton; Leigh F. Jones; Pippa Kett; Rolf Kraehenbuehl; Patrick J. Murphy; Graham J. Tizzard; Niles B. Willmore; Oliver T. Wright

doi:10.3390/reactions5030027

C 2 -Symmetric Amino Acid Amide-Derived Organocatalysts †

Zahraa S. Al-Taie, Simon J. Coles, Aileen Congreve, Dylan Ford, Lucy Green, Peter N. Horton, Leigh F. Jones, Pippa Kett, Rolf Kraehenbuehl, Patrick J. Murphy, Graham J. Tizzard, Niles B. Willmore, Oliver T. Wright

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

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.

Original language	English
Pages (from-to)	567-586
Number of pages	20
Journal	Reactions
Volume	5
Issue number	3
DOIs	https://doi.org/10.3390/reactions5030027
Publication status	Published - 24 Aug 2024

Keywords

amino acids
organocatalysis
Michael additions
aldol reactions

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10.3390/reactions5030027Licence: CC BY

reactions-05-00027Final published version, 2.07 MBLicence: CC BY

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title = "C 2 -Symmetric Amino Acid Amide-Derived Organocatalysts †",

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.",

keywords = "amino acids, organocatalysis, Michael additions, aldol reactions",

author = "Al-Taie, \{Zahraa S.\} and Coles, \{Simon J.\} and Aileen Congreve and Dylan Ford and Lucy Green and Horton, \{Peter N.\} and Jones, \{Leigh F.\} and Pippa Kett and Rolf Kraehenbuehl and Murphy, \{Patrick J.\} and Tizzard, \{Graham J.\} and Willmore, \{Niles B.\} and Wright, \{Oliver T.\}",

year = "2024",

month = aug,

day = "24",

doi = "10.3390/reactions5030027",

language = "English",

volume = "5",

pages = "567--586",

journal = "Reactions",

issn = "2624-781X",

publisher = "MDPI",

number = "3",

}

TY - JOUR

T1 - C 2 -Symmetric Amino Acid Amide-Derived Organocatalysts †

AU - Al-Taie, Zahraa S.

AU - Coles, Simon J.

AU - Congreve, Aileen

AU - Ford, Dylan

AU - Green, Lucy

AU - Horton, Peter N.

AU - Jones, Leigh F.

AU - Kett, Pippa

AU - Kraehenbuehl, Rolf

AU - Murphy, Patrick J.

AU - Tizzard, Graham J.

AU - Willmore, Niles B.

AU - Wright, Oliver T.

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.

KW - amino acids

KW - organocatalysis

KW - Michael additions

KW - aldol reactions

U2 - 10.3390/reactions5030027

DO - 10.3390/reactions5030027

M3 - Article

SN - 2624-781X

VL - 5

SP - 567

EP - 586

JO - Reactions

JF - Reactions

IS - 3

ER -

C 2 -Symmetric Amino Acid Amide-Derived Organocatalysts †

Abstract

Keywords

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