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. [reaction: see text]
Han
Zhengxu
Z
Chemical Process Research and Development, Sepracor Inc., 84 Waterford Drive, Marlborough, MA 01752, USA.
Krishnamurthy
Dhileepkumar
D
Pflum
Derek
D
Grover
Paul
P
Wald
Stephen A
SA
Senanayake
Chris H
CH
D003503:Cyclobutanes / Q000138:chemical synthesis*; D006017:Glycolipids / Q000737:chemistry* / Q000302:isolation & purification; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D003503:Cyclobutanes; D006017:Glycolipids; D007202:Indicators and Reagents; C469708:caminoside A; C058254:sibutramine