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 an...

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Autores principales: Al-Taie, Zahraa S., Anetts, Simon R., 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., Wilson, Jack A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054603/
https://www.ncbi.nlm.nih.gov/pubmed/35514555
http://dx.doi.org/10.1039/c9ra07508a
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author Al-Taie, Zahraa S.
Anetts, Simon R.
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.
Wilson, Jack A.
author_facet Al-Taie, Zahraa S.
Anetts, Simon R.
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.
Wilson, Jack A.
author_sort Al-Taie, Zahraa S.
collection PubMed
description 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.
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spelling pubmed-90546032022-05-04 Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study Al-Taie, Zahraa S. Anetts, Simon R. 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. Wilson, Jack A. RSC Adv Chemistry 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. The Royal Society of Chemistry 2020-06-11 /pmc/articles/PMC9054603/ /pubmed/35514555 http://dx.doi.org/10.1039/c9ra07508a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Al-Taie, Zahraa S.
Anetts, Simon R.
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.
Wilson, Jack A.
Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
title Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
title_full Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
title_fullStr Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
title_full_unstemmed Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
title_short Proline derived guanidine catalysts forge extensive H-bonded architectures: a solution and solid state study
title_sort proline derived guanidine catalysts forge extensive h-bonded architectures: a solution and solid state study
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054603/
https://www.ncbi.nlm.nih.gov/pubmed/35514555
http://dx.doi.org/10.1039/c9ra07508a
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