title: Stereoselective radical addition of an acetal to sterically tuned enantiomerically pure N-sulfinyl imines.
abstract: Enantiomerically enriched sulfonamides were synthesized by the radical addition of an acetal to enantiomerically pure N-sulfinyl imines using dimethylzinc-air and boron trifluoride diethyl etherate. Higher levels of stereocontrol were observed by using a mesitylenesulfinyl group. Furthermore, an amine and an amino alcohol with high enantiomeric purity were obtainable from the sulfonamide product.
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: Ken-ichi
authors.initials: K
authors.lastname: Yamada
authors.forename: Takumi
authors.initials: T
authors.lastname: Sejima
authors.forename: Masaru
authors.initials: M
authors.lastname: Maekawa
authors.forename: Yasutomo
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Mayu
authors.initials: M
authors.lastname: Nakano
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tomioka
mesh_terms: D000080:Acetals / Q000138:chemical synthesis / Q000737:chemistry*; D001880:Boranes / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000080:Acetals; D001880:Boranes; D007097:Imines; D009942:Organometallic Compounds; D013449:Sulfonamides; C101707:boron trifluoride etherate; C511262:dimethylzinc