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

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.