Synthesis of Enantiomerically Pure <i>anti</i>-1,2-Diaryl and <i>syn</i>-1,2-Alkylaryl <i>vic</i>-Selenoamines

Abstract

Phenylselenyl benzylcarbanion stabilized by an (<i>S</i>)-2-<i>p</i>-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (<i>S</i>)-<i>N</i>-(<i>p</i>-tolylsulfinyl)­imines at −98 °C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The <i>syn</i> or <i>anti</i> relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1<i>R</i>,2<i>S</i>)-1-aryl­[or (1<i>S</i>,2<i>S</i>)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with <i>t-</i>BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA