Organocatalysis: Cinchona catalysts

The resurgence of asymmetric organocatalysis has been accompanied by the development of countless synthetic methodologies making use of Cinchona alkaloids (or their derivatives) as catalysts. Although important steps have been made in the understanding of the mode of action of this class of compounds, the development of new catalytic methodologies is largely carried out using experiment-driven approaches. This overview presents a selection of computational results on the behavior of Cinchona alkaloids with respect to their structure, the way they interact with other species, and, ultimately, their catalytic activity. The twofold aim of this contribution is to provide organic chemists with accessible information on computational results as well as to present theoretical chemists an overview of the methods commonly used to model Cinchona organocatalysts, and how they are comparable to experimental results. (C) 2011 John Wiley & Sons, Ltd. WIREs Comput Mol Sci 2011 1 142-152 DOI:10.1002/wcms.2