Case Study Through the Chiralpedia Lens: tert-Butanesulfinamide — The Sulfur-Centered Chiral Tool That Changed Drug Synthesis
A Quiet Revolution in Asymmetric Synthesis tert-Butanesulfinamide, widely known as Ellman’s sulfinamide, is one of the most influential chiral auxiliaries in modern asymmetric synthesis. Developed in the 1990s by the laboratory of Jonathan Ellman, this sulfur-centered chiral reagent revolutionized the stereoselective construction of amines—key structural motifs in pharmaceuticals and agrochemicals. Its configurationally stable stereogenic sulfur atom enables the formation of N-sulfinyl imines that undergo highly diastereoselective nucleophilic additions, providing reliable access to enantioenriched primary and …