Continuum of Mechanisms for Nucleophilic Substitutions of Cyclic Acetals

摘要

The effect of nucleophile strength on diastereoselectivity in the nucleophilic substitution of cyclic acetals was explored. Stereoselectivity remained constant and high as nucleophilicity increased until a threshold value was reached. Beyond this point, however, selection of Lewis acid determined whether stereochemical inversion or erosion was observed.