title: Asymmetric radical addition of ethers to enantiopure N-p-toluenesulfinyl aldimines, mediated by dimethylzinc-air.
abstract: Asymmetric radical addition of ethers to enantiopure aromatic N-p-toluenesulfinyl aldimines has been achieved. The requisite radicals were generated by dimethylzinc-air. Lewis acid activation of the N-p-toluenesulfinyl aldimines followed by radical addition gives a mixture of sulfinamide and sulfonamide products. Subsequent treatment of the mixture with dry m-CPBA affords the sulfonamide product in enantiomerically enriched form. [reaction: see text]
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Tito
authors.initials: T
authors.lastname: Akindele
authors.forename: Yasutomo
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Masaru
authors.initials: M
authors.lastname: Maekawa
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Umeki
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Yamada
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tomioka
mesh_terms: D000388:Air; D002851:Chromatography, High Pressure Liquid; D004987:Ethers / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*; D013449:Sulfonamides; D014050:Toluene / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D004987:Ethers; D005609:Free Radicals; D007097:Imines; D009942:Organometallic Compounds; D013441:Sulfinic Acids; D013449:Sulfonamides; D014050:Toluene; C511262:dimethylzinc