Synthesis of Optically Pure <i>vic</i>-Sulfanyl Amines Mediated by a Remote Sulfinyl Group

Enantiomerically pure <i>syn</i>-1,2-diaryl-1,2-sulfanylamine derivatives can be obtained in a completely stereoselective manner by reaction of the benzylcarbanion Li-(<i>S</i>)-<b>1</b> with <i>N</i>-phenyl (or PMP)-arylidene aldimines and further desulfinylation with <i>t</i>-BuLi. Theoretical studies at the DFT (mPW1PW91) level with the CPCM model, by using the Gaussian09 program, provide a good explanation for the stereochemical results.