Estimating the Stereoinductive Potential of Cinchona Alkaloids with a Prochiral Probe Approach.

Cinchona alkaloids occupy a privileged status due to their optimal possession of two desirable properties, namely catalytic efficiency and stereoselectivity. This paper proposes a new quantitative measure, the energy difference between the adducts formed by reand siface attack to Mosher’s cation (ΔMOSCAre−si) as a measure of stereoinductive potential, by taking the example of cinchona alkaloids. Other descriptors such as methyl cation affinities and the one based on continuous symmetry measures are also estimated and correlated with ΔMOSCAre−sivalues. [ABSTRACT FROM AUTHOR]