title: N-Carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides.
abstract: [reaction: see text] Simply mixing amino alcohol A and thiol in toluene and TFA provided the corresponding amino sulfide B in excellent chemical yield and diastereoselectivity. A double SN2 process initiated by O-5 participation of the neighboring N-carbamate group was advanced to explain the overall retention of configuration at the chiral benzylic center.
authors.affiliation: Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
authors.forename: Michaël
authors.initials: M
authors.lastname: De Paolis
authors.forename: Jörg
authors.initials: J
authors.lastname: Blankenstein
authors.forename: Michèle
authors.initials: M
authors.lastname: Bois-Choussy
authors.forename: Jieping
authors.initials: J
authors.lastname: Zhu
mesh_terms: D000588:Amines / Q000138:chemical synthesis*; D000818:Animals; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D002219:Carbamates / Q000737:chemistry*; D006868:Hydrolysis; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis*
chemical_list: D000588:Amines; D001593:Benzyl Compounds; D002219:Carbamates; D007202:Indicators and Reagents; D013440:Sulfides