First Application of Tunable Alkyl or Aryl Sulfinamides to the Stereoselective Synthesis of a Chiral Amine: Asymmetric Synthesis of (<i>R</i>)-Didesmethylsibutramine ((<i>R</i>)-DDMS) Using (<i>R)</i>-Triethylmethylsulfinamide ((<i>R</i>)-TESA)

Abstract

A highly diastereoselective addition of i-BuLi to a triethylmethylsulfinamide derived aldimine was used as the key step in the first asymmetric synthesis of (R)-didesmethylsibutramine, a metabolite of sibutramine for the potential treatment of CNS disorders. [reaction: see text]