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

Al-Nahrain University
University of Southampton
Durham University
Bangor University
The University of Wolverhampton

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

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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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