Enantioselective nucleophilic opening of meso epoxides by organolithium reagents

Abstract

Aryl lithium reagents, complexed with (-)-sparteine, react enantioselectively with cyclic meso epoxides, to afford chiral aryl cyclanols. The enantiomeric excess, though moderate (27-87%), is the best in the literature for such a reaction. Activation by BF3.OEt2 is needed, and is compatible with a diamine such as (-)-sparteine.