Stereospecific nucleophilic substitution at quaternary carbon stereocenters of cyclopropyl carbinols

Stereospecific nucleophilic substitution is a powerful tool for the preparation of diastereo- and enantiomerically enriched compounds. Due to the intrinsic difficulty of selective cleavage of a C–C σ-bond combined with the high stereocontrol required at a congested carbon, the unprecedented stereospecific nucleophilic substitution at a quaternary carbon stereocenter is a rather challenging but fascinating transformation. Recently, a strategy that utilizes the exergonic ring opening of polysubstituted stereodefined cyclopropyl derivatives bearing quaternary carbon stereocenters was conceived to realize this goal with a complete inversion of configuration. In this perspective, we will detail the advances in this area, while stating current challenges and future directions.