Estimating the stereoinductive potential of cinchona alkaloids with a prochiral probe approach

Abstract

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 re and si face attack to Mosher’s cation (ΔMOSCA_re−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 ΔMOSCA_re−si values.