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Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study

Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study

The preparation of a range of amino acid derived guanidine organocatalysts is reported together with their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 56%. Some insight into the mechanism was sought by using X-ray crystallography and a detailed study of the intra- and intermolecular hydrogen bonding is reported. This journal is

2046-2069
22397-22416
Al-Taie, Zahraa S.
07181947-5786-4d1e-ac8e-7a532d692934
Al-Taie, Zahraa S.
07181947-5786-4d1e-ac8e-7a532d692934
Anetts, Simon R.
38c98182-3228-48be-b5fb-04a8fbdf1fb9
Christensen, Jeppe
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Christensen, Jeppe
f37d3a1e-05d9-4144-8af2-bd29ead7d9c3
Coles, Simon J.
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Horton, Peter N.
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Evans, Daniel M.
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Jones, Leigh F.
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De Kleijne, Frank F.J.
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Ledbetter, Shaun M.
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Mehdar, Yassin T.H.
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Murphy, Patrick J.
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Wilson, Jack A.
1b8508ca-f2a3-4774-983a-33ff1fd3e8fe
Al-Taie, Zahraa S.
07181947-5786-4d1e-ac8e-7a532d692934
Al-Taie, Zahraa S.
07181947-5786-4d1e-ac8e-7a532d692934
Anetts, Simon R.
38c98182-3228-48be-b5fb-04a8fbdf1fb9
Christensen, Jeppe
f37d3a1e-05d9-4144-8af2-bd29ead7d9c3
Christensen, Jeppe
f37d3a1e-05d9-4144-8af2-bd29ead7d9c3
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Horton, Peter N.
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Evans, Daniel M.
097189a5-9c0b-4774-a48a-3a04e02c6f07
Jones, Leigh F.
fdb8562f-36c2-4f8f-9221-947e1d05a45e
De Kleijne, Frank F.J.
a552e459-1c55-4186-90c3-be2d631ad8a8
Ledbetter, Shaun M.
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Mehdar, Yassin T.H.
150b7123-5140-4a14-8b2a-8a49de83cd57
Murphy, Patrick J.
5ab567ae-c42c-44d4-8ae4-8b376cf2e6e6
Wilson, Jack A.
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Al-Taie, Zahraa S., Al-Taie, Zahraa S., Anetts, Simon R., Christensen, Jeppe, Christensen, Jeppe, Coles, Simon J., Horton, Peter N., Evans, Daniel M., Jones, Leigh F., De Kleijne, Frank F.J., Ledbetter, Shaun M., Mehdar, Yassin T.H., Murphy, Patrick J. and Wilson, Jack A. (2020) Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study. RSC Advances, 10 (38), 22397-22416. (doi:10.1039/c9ra07508a).

Record type: Article

Abstract

The preparation of a range of amino acid derived guanidine organocatalysts is reported together with their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 56%. Some insight into the mechanism was sought by using X-ray crystallography and a detailed study of the intra- and intermolecular hydrogen bonding is reported. This journal is

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Accepted/In Press date: 25 February 2020
Published date: 11 June 2020

Identifiers

Local EPrints ID: 442825
URI: http://eprints.soton.ac.uk/id/eprint/442825
ISSN: 2046-2069
PURE UUID: bfec732e-401d-4df3-b694-63004f655259
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Peter N. Horton: ORCID iD orcid.org/0000-0001-8886-2016

Catalogue record

Date deposited: 28 Jul 2020 16:31
Last modified: 26 Nov 2021 02:43

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Contributors

Author: Zahraa S. Al-Taie
Author: Zahraa S. Al-Taie
Author: Simon R. Anetts
Author: Jeppe Christensen
Author: Jeppe Christensen
Author: Simon J. Coles ORCID iD
Author: Peter N. Horton ORCID iD
Author: Daniel M. Evans
Author: Leigh F. Jones
Author: Frank F.J. De Kleijne
Author: Shaun M. Ledbetter
Author: Yassin T.H. Mehdar
Author: Patrick J. Murphy
Author: Jack A. Wilson

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