Simply mixing amino alc. I (R = substituent) and thiols in toluene and TFA provided the corresponding amino sulfide II in excellent chem. 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. [on SciFinder (R)]
Title
N-Carbamate-Assisted Stereoselective Synthesis of Chiral Vicinal Amino Sulfides
Published in
Organic Letters
Volume
4
Issue
7
Pages
1235-1238
Date
2002
ISSN
1523-7060
Note
CAN 136:385902
25-9
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
75-66-1; 623-51-8; 2365-48-2; 20756-86-9; 53907-28-1; 426213-61-8; 426213-63-0; 426213-64-1; 426213-65-2; 426213-72-1; 426213-75-4; 426213-77-6; 426213-78-7 Role: RCT (Reactant), RACT (Reactant or reagent) (N-carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides); 426213-68-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (N-carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides); 426213-66-3P; 426213-67-4P; 426213-69-6P; 426213-70-9P; 426213-71-0P; 426213-73-2P; 426213-74-3P; 426213-76-5P; 426213-79-8P; 426213-80-1P; 426213-81-2P Role: SPN (Synthetic preparation), PREP (Preparation) (N-carbamate-assisted stereoselective synthesis of chiral vicinal amino sulfides)
Record creation date
2010-11-25
