C(2)-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones

C(2)-symmetric bisamidines 8 have been tested as chiral Brønsted bases in the Diels-Alder reaction of anthrones and N-substituted maleimides. High yields of cycloadducts and significant asymmetric inductions up to 76% ee are accessible. The proposed mechanism involves proton transfer between anthron...

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Detalles Bibliográficos
Autores principales: Akalay, Deniz, Dürner, Gerd, Bats, Jan W, Göbel, Michael W
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2008
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2533436/
https://www.ncbi.nlm.nih.gov/pubmed/18941500
http://dx.doi.org/10.3762/bjoc.4.28
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author Akalay, Deniz
Dürner, Gerd
Bats, Jan W
Göbel, Michael W
author_facet Akalay, Deniz
Dürner, Gerd
Bats, Jan W
Göbel, Michael W
author_sort Akalay, Deniz
collection PubMed
description C(2)-symmetric bisamidines 8 have been tested as chiral Brønsted bases in the Diels-Alder reaction of anthrones and N-substituted maleimides. High yields of cycloadducts and significant asymmetric inductions up to 76% ee are accessible. The proposed mechanism involves proton transfer between anthrone and bisamidine, association of the resulting ions and finally a cycloaddition step stereoselectively controlled by the chiral ion pair.
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spelling pubmed-25334362008-10-20 C(2)-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones Akalay, Deniz Dürner, Gerd Bats, Jan W Göbel, Michael W Beilstein J Org Chem Full Research Paper C(2)-symmetric bisamidines 8 have been tested as chiral Brønsted bases in the Diels-Alder reaction of anthrones and N-substituted maleimides. High yields of cycloadducts and significant asymmetric inductions up to 76% ee are accessible. The proposed mechanism involves proton transfer between anthrone and bisamidine, association of the resulting ions and finally a cycloaddition step stereoselectively controlled by the chiral ion pair. Beilstein-Institut 2008-08-07 /pmc/articles/PMC2533436/ /pubmed/18941500 http://dx.doi.org/10.3762/bjoc.4.28 Text en Copyright © 2008, Akalay et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Akalay, Deniz
Dürner, Gerd
Bats, Jan W
Göbel, Michael W
C(2)-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones
title C(2)-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones
title_full C(2)-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones
title_fullStr C(2)-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones
title_full_unstemmed C(2)-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones
title_short C(2)-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones
title_sort c(2)-symmetric bisamidines: chiral brønsted bases catalysing the diels-alder reaction of anthrones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2533436/
https://www.ncbi.nlm.nih.gov/pubmed/18941500
http://dx.doi.org/10.3762/bjoc.4.28
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