Recent progress in asymmetric rearrangement reactions mediated by chiral Brønsted acids

Abstract

Rearrangement reactions, a fundamental tool for constructing complex molecules, offer an atom-economical approach to target molecule synthesis. Chiral acid-mediated rearrangement reactions provide a powerful tool for the synthesis of enantioenriched molecules, crucial for synthesizing natural products, developing new drugs, and constructing functional materials. Herein we have categorized the 15 chiral Brønsted acid mediated rearrangements based on the rearrangement mode, such as C–C bond cleavage/formation, skeletal rearrangements, and migration reactions. This review can delve deeper into specific examples within each rearrangement type, highlighting the reaction mechanisms, catalyst design strategies, and substrate scope. Additionally, this review provides a systematic analysis of chiral Brønsted acid catalysis in rearrangement reactions, highlighting its unique value and contribution to the field of asymmetric synthesis. We believe that this review can offer valuable insights into the application of chiral Brønsted acid catalysis in rearrangement reactions, a topic of significant interest to both medical and synthetic organic chemists.