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