N-Carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides.
[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.
De Paolis
Michaël
M
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Blankenstein
Jörg
J
Bois-Choussy
Michèle
M
Zhu
Jieping
J
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*
D000588:Amines; D001593:Benzyl Compounds; D002219:Carbamates; D007202:Indicators and Reagents; D013440:Sulfides