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We thank Evonik Degussa and the DFG (Priority Programme Organocatalysis) for financial support, as well as the Fonds der Chemischen Industrie for a scholarship awarded to A.K.
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Communication
Highly Enantioselective Organocatalytic Carbonyl-Ene Reaction with Strongly Acidic, Chiral Brønsted Acids as Efficient Catalysts†
Article first published online: 24 JUL 2008
DOI: 10.1002/anie.200802139
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Rueping, M., Theissmann, T., Kuenkel, A. and Koenigs, René M. (2008), Highly Enantioselective Organocatalytic Carbonyl-Ene Reaction with Strongly Acidic, Chiral Brønsted Acids as Efficient Catalysts. Angew. Chem. Int. Ed., 47: 6798–6801. doi: 10.1002/anie.200802139
- †
Publication History
- Issue published online: 20 AUG 2008
- Article first published online: 24 JUL 2008
- Manuscript Received: 7 MAY 2008
Funded by
- DFG
Keywords:
- asymmetric catalysis;
- Brønsted acids;
- carbonyl-ene reaction;
- ion pairs;
- organocatalysis
You can count on the counterion in ion-pair intermediates to induce high levels of asymmetry in the title reaction. The efficient transformation proceeds under mild reaction conditions in the presence of an air-stable N-triflylphosphoramide in a low catalyst loading of just 1 mol % to give substituted α-hydroxyesters in good yields and with excellent ee values (see scheme; R=aryl).