2006/08/24 by Franklin A. Davis · 1 citation
Chemistry · #Synthesis and Catalytic Reactions #Asymmetric Synthesis and Catalysis #Synthetic Organic Chemistry Methods #Chemistry #Reagent #Stereocenter #Sulfur #Oxidizing agent #Nitrogen #Organic chemistry #Organosulfur compounds #Sulfoxide #Carbon fibers #Enantioselective synthesis #Combinatorial chemistry #Catalysis
paper · doi:10.1021/jo061027p
openalex publication_date 2006/08/24 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/30
This account reviews our efforts over the past 37 years to understand the chemistry of a select group of sulfur-nitrogen compounds including sulfinimines (N-sulfinyl imines) and N-sulfonyloxaziridines. Our early exploration of the thermal properties of sulfenamides, a class of sulfur-nitrogen compounds about which little was known, resulted in a new procedure, the silver-assisted method, for the construction of sulfenimines (N-sulfenyl imines). Selective oxidations of these compounds resulted in the production of N-sulfinyl imines (sulfinimines) and N-sulfonyloxaziridines. N-Sulfonyloxaziridines turned out to be a new class of aprotic neutral oxidizing reagents. Enantiomerically pure examples afford high ee values in the oxidation of enolates to alpha-hydroxy carbonyl compounds and in the oxidation of sulfides and selenides to sulfoxides and selenoxides. Additions of organometallic reagents to enantiomerically pure sulfinimines provide the best and most versatile method for the asymmetric construction of the carbon-nitrogen stereocenters found in many biologically active compounds. Sulfinimine-derived chiral building blocks provide efficient access to many classes of nitrogen heterocycles including aziridines, 2H-azirines, pyrrolidines, and piperidines.