title: Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine.
abstract: [reaction: see text] The asymmetric synthesis and chemical modification of p-bromophenyl methyl sulfoximine (2) is described. Starting from p-bromophenyl menthyl sulfinate (5), enantiopure 2 can be obtained in a short reaction sequence involving a well-established substitution reaction followed by stereospecific imination with O-mesitylenesulfonylhydroxylamine (MSH). Palladium-catalyzed Buchwald/Hartwig, Suzuki, and Stille coupling reactions allow a broad variation of the sulfoximine aryl group, which is otherwise difficult to achieve. The incorporation of a p-morpholino-substituted derivative into a pseudotripeptide demonstrates the applicability of the novel sulfoximine derivatives.
authors.affiliation: Institut für Organische Chemie der RWTH Aachen, Professor-Pirlet-Str. 1, D-52056 Aachen, Germany.
authors.forename: Gae Young
authors.initials: GY
authors.lastname: Cho
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Okamura
authors.forename: Carsten
authors.initials: C
authors.lastname: Bolm
mesh_terms: D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C500923:(S)-gamma-fluoroleucine ethyl ester; D004952:Esters; D010165:Palladium; D007930:Leucine