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.
Author:Deniz AkalayGND, Gerd DürnerGND, Jan W. Bats, Michael GöbelORCiDGND
Pubmed Id:https://pubmed.ncbi.nlm.nih.gov/18941500
Parent Title (English):Beilstein journal of organic chemistry
Publisher:Beilstein-Institut zur Förderung der Chemischen Wissenschaften
Place of publication:Frankfurt, Main
Document Type:Article
Year of Completion:2008
Date of first Publication:2008/08/07
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2008/09/25
Tag:Asymmetric Catalysis; Bisamidines; Brønsted base; Diels- Alder reaction; Organocatalysis
Page Number:6
First Page:1
Last Page:6
© 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)
Source:Beilstein Journal of Organic Chemistry 2008, 4, No. 28. ; doi:10.3762/bjoc.4.28
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - Namensnennung 2.0