Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine.
[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.
Cho
Gae Young
GY
Institut für Organische Chemie der RWTH Aachen, Professor-Pirlet-Str. 1, D-52056 Aachen, Germany.
Okamura
Hiroaki
H
Bolm
Carsten
C
D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D007930:Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
C500923:(S)-gamma-fluoroleucine ethyl ester; D004952:Esters; D010165:Palladium; D007930:Leucine