Opportunities for the Application and Advancement of the Corey–Chaykovsky Cyclopropanation

Cyclopropanes are a common motif in many pharmaceutically relevant compounds, and methods for the synthesis of these strained rings have relevance throughout the pharmaceutical development process. Among the many options, the Corey–Chaykovsky cyclopropanation stands out due to its broad substrate scope, high functional group tolerance, and mild conditions. Despite these benefits, its application to the synthesis of cyclopropanes, specifically in the context of large-scale syntheses, has been limited. In this review, the scope and limitations of the Brønsted-base-promoted Corey–Chaykovsky cyclopropanation with sulfur ylides will be examined. Through this discussion, gaps in the scope and understanding of the transformation will be highlighted to promote further application and advancement of this powerful and useful methodology.