TY - JOUR A1 - Akalay, Deniz A1 - Dürner, Gerd A1 - Bats, Jan W. A1 - Göbel, Michael T1 - C2-symmetric bisamidines : chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones T2 - Beilstein journal of organic chemistry N2 - 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. KW - Asymmetric Catalysis KW - Bisamidines KW - Brønsted base KW - Diels- Alder reaction KW - Organocatalysis Y1 - 2008 UR - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/5844 UR - https://nbn-resolving.org/urn:nbn:de:hebis:30-57841 SN - 1860-5397 N1 - © 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) VL - 4 IS - 28 SP - 1 EP - 6 PB - Beilstein-Institut zur Förderung der Chemischen Wissenschaften CY - Frankfurt, Main ER -