C2-symmetric bisamidines : chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones

C2-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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Metadaten
Author:Deniz Akalay, Gerd Dürner, Jan W. Bats, Michael W. Göbel
URN:urn:nbn:de:hebis:30-57841
Document Type:Article
Language:English
Date of Publication (online):25.09.2008
Year of first Publication:2008
Publishing Institution:Univ.-Bibliothek Frankfurt am Main
Tag:Asymmetric Catalysis ; Bisamidines ; Brønsted base ; Diels- Alder reaction ; Organocatalysis
Source:Beilstein Journal of Organic Chemistry 2008, 4, No. 28. ; doi:10.3762/bjoc.4.28
HeBIS PPN:205902820
Institutes:Biochemie und Chemie
Dewey Decimal Classification:540 Chemie und zugeordnete Wissenschaften
Sammlungen:Universitätspublikationen
Note:
© 2008 Akalay et al; licensee Beilstein-Institut.
This is an Open Access article under the terms of the Creative Commons Attribution License (http://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: (http://www.beilstein- journals.org/bjoc)
Licence (German):License LogoCreative Commons - Namensnennung 2.0

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