This work was supported by Aarhus University, FNU, and the Carlsberg Foundation. C.R.-E. thanks the Generalitat de Catalunya for a Beatriu de Pinós postdoctoral fellowship. Dr. Jacob Overgaard is acknowledged for performing X-ray analysis.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/olbannercenter.gif?v=1&s=c083e1920cd41ed129901c116018eab93b5ad3c4)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
Organocatalytic Activation of Polycyclic Aromatic Compounds for Asymmetric Diels–Alder Reactions†
Article first published online: 13 SEP 2012
DOI: 10.1002/anie.201205836
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 51, Issue 41, pages 10271–10274, October 8, 2012
Additional Information
How to Cite
Jiang, H., Rodríguez-Escrich, C., Johansen, T. K., Davis, R. L. and Jørgensen, K. A. (2012), Organocatalytic Activation of Polycyclic Aromatic Compounds for Asymmetric Diels–Alder Reactions . Angew. Chem. Int. Ed., 51: 10271–10274. doi: 10.1002/anie.201205836
- †
Publication History
- Issue published online: 1 OCT 2012
- Article first published online: 13 SEP 2012
- Manuscript Received: 23 JUL 2012
Funded by
- Aarhus University
- FNU
- Carlsberg Foundation
Keywords:
- anthracene activation;
- aromaticity;
- asymmetric catalysis;
- Diels–Alder reaction;
- organocatalysis
The anglerfish catalyst: The activation of anthracenes through aminocatalysis (see scheme) allows them to undergo [4+2] cycloadditions with concomitant breaking of the aromaticity at room temperature and low catalyst loadings. A highly enantioselective Diels–Alder reaction of anthracenes has been developed using nitroalkenes as dienophiles.