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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Detalles Bibliográficos
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
Descripción
Sumario: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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