title: Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2,4,6-trimethylphenylsulfinamide.
abstract: The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
authors.forename: Franklin A
authors.initials: FA
authors.lastname: Davis
authors.forename: Tokala
authors.initials: T
authors.lastname: Ramachandar
authors.forename: Yongzhong
authors.initials: Y
authors.lastname: Wu
mesh_terms: D001388:Aziridines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis*
chemical_list: D001388:Aziridines; D007202:Indicators and Reagents; D063065:Organophosphonates; D013452:Sulfonium Compounds