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N-carbamate protected amino acid derived guanidine organocatalysts

N-carbamate protected amino acid derived guanidine organocatalysts
N-carbamate protected amino acid derived guanidine organocatalysts
We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest that the C2-symmetric catalysts are lead compounds for the further development of this methodology.
Amino acids, Guanidines, H-bonded extended networks, Organocatalysis
0040-4020
Al-Taie, Zahraa S.
07181947-5786-4d1e-ac8e-7a532d692934
Anderson, Joseph M.
a0f7991c-48ff-4702-b31b-6fc5afa0c9e4
Bischoff, Laura
04c750d7-d925-47ad-9427-5c4cc952045c
Christensen, Jeppe
86c5d846-78b8-490a-b663-5eb5ca10c0ae
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Froom, Richard
8c54d8d2-ba49-42ad-8609-8ccd349d9f4e
Gibbard, Mari E.
2c6a85f8-40e2-44d4-948f-b9b1d1a4f599
Jones, Leigh F.
fdb8562f-36c2-4f8f-9221-947e1d05a45e
De Kleijne, Frank F.J.
a552e459-1c55-4186-90c3-be2d631ad8a8
Murphy, Patrick J.
5ab567ae-c42c-44d4-8ae4-8b376cf2e6e6
Thompson, Emma C.
4ae488d8-2d99-460c-9b39-ac099c024080
Al-Taie, Zahraa S.
07181947-5786-4d1e-ac8e-7a532d692934
Anderson, Joseph M.
a0f7991c-48ff-4702-b31b-6fc5afa0c9e4
Bischoff, Laura
04c750d7-d925-47ad-9427-5c4cc952045c
Christensen, Jeppe
86c5d846-78b8-490a-b663-5eb5ca10c0ae
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Froom, Richard
8c54d8d2-ba49-42ad-8609-8ccd349d9f4e
Gibbard, Mari E.
2c6a85f8-40e2-44d4-948f-b9b1d1a4f599
Jones, Leigh F.
fdb8562f-36c2-4f8f-9221-947e1d05a45e
De Kleijne, Frank F.J.
a552e459-1c55-4186-90c3-be2d631ad8a8
Murphy, Patrick J.
5ab567ae-c42c-44d4-8ae4-8b376cf2e6e6
Thompson, Emma C.
4ae488d8-2d99-460c-9b39-ac099c024080

Al-Taie, Zahraa S., Anderson, Joseph M., Bischoff, Laura, Christensen, Jeppe, Coles, Simon J., Froom, Richard, Gibbard, Mari E., Jones, Leigh F., De Kleijne, Frank F.J., Murphy, Patrick J. and Thompson, Emma C. (2021) N-carbamate protected amino acid derived guanidine organocatalysts. Tetrahedron, 89, [132093]. (doi:10.1016/j.tet.2021.132093).

Record type: Article

Abstract

We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest that the C2-symmetric catalysts are lead compounds for the further development of this methodology.

Text
Revised Tetrahedron resubmission 2021 changes accepted and footnote added - Accepted Manuscript
Available under License Creative Commons Attribution Non-commercial No Derivatives.
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Accepted/In Press date: 17 March 2021
e-pub ahead of print date: 2 April 2021
Published date: 4 June 2021
Additional Information: Funding Information: We would like to than Dr Daniel Evans for his invaluable help with this project, the BEACON II scheme (ERDF; PJM) and the Iraqi government (ZSSA-T). We also thank the EPSRC National Crystallography Service at the University of Southampton and Rolf Kraehenbuehl (Bangor University, Centre for Environmental Biotechnology Project part-funded by the European Regional Development Fund (ERDF) through the Welsh Government) for MS data. Funding Information: We would like to than Dr Daniel Evans for his invaluable help with this project, the BEACON II scheme (ERDF; PJM) and the Iraqi government (ZSSA-T). We also thank the EPSRC National Crystallography Service at the University of Southampton and Rolf Kraehenbuehl (Bangor University, Centre for Environmental Biotechnology Project part-funded by the European Regional Development Fund (ERDF) through the Welsh Government) for MS data. Publisher Copyright: © 2021
Keywords: Amino acids, Guanidines, H-bonded extended networks, Organocatalysis
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Identifiers

Local EPrints ID: 448968
URI: http://eprints.soton.ac.uk/id/eprint/448968
DOI: doi:10.1016/j.tet.2021.132093
ISSN: 0040-4020
PURE UUID: 49caa1b1-ebe6-4c1d-82d7-138224ae1b27
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 12 May 2021 16:31
Last modified: 17 Mar 2024 06:33

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Contributors

Author: Zahraa S. Al-Taie
Author: Joseph M. Anderson
Author: Laura Bischoff
Author: Jeppe Christensen
Author: Simon J. Coles ORCID iD
Author: Richard Froom
Author: Mari E. Gibbard
Author: Leigh F. Jones
Author: Frank F.J. De Kleijne
Author: Patrick J. Murphy
Author: Emma C. Thompson

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