This work was supported by the National Science Foundation through a CAREER award to M.S.S. (CHE-132905). M.S.S. thanks the Dreyfus foundation (Teacher-Scholar) and Pfizer for their support.
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Systematically Probing the Effect of Catalyst Acidity in a Hydrogen-Bond-Catalyzed Enantioselective Reaction†
Article first published online: 14 MAY 2007
DOI: 10.1002/anie.200700298
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Jensen, K. and Sigman, M. (2007), Systematically Probing the Effect of Catalyst Acidity in a Hydrogen-Bond-Catalyzed Enantioselective Reaction. Angewandte Chemie International Edition, 46: 4748–4750. doi: 10.1002/anie.200700298
- †
Publication History
- Issue published online: 11 JUN 2007
- Article first published online: 14 MAY 2007
- Manuscript Revised: 15 MAR 2007
- Manuscript Received: 22 JAN 2007
Funded by
- National Science Foundation. Grant Number: CHE-132905
Keywords:
- asymmetric catalysis;
- cycloaddition;
- enantioselectivity;
- hydrogen bonds;
- linear free energy relationships
Graphical Abstract
Defining the relationship: The effect of catalyst acidity has been systematically probed by using a modular oxazoline catalyst in a hetero-Diels–Alder reaction catalyzed by hydrogen bonding. Linear free energy relationships were observed between the catalyst acidity and both the reaction rate and enantioselectivity (see picture).