Synthesis and Palladium-Catalyzed Coupling Reactions of Enantiopure p-Bromophenyl Methyl Sulfoximine

• Published in: Journal of organic chemistry Vol. 70; no. 6; pp. 2346 - 2349
• Main Authors: Cho, Gae Young, Okamura, Hiroaki, Bolm, Carsten
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.03.2005; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Esters - chemical synthesis; Exact sciences and technology; Leucine - analogs & derivatives; Leucine - chemical synthesis; Molecular Conformation; Noncondensed benzenic compounds; Organic chemistry; Palladium - chemistry; Peptides; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; REAGENTS; LIGANDS; ROUTES; SULFIDES; RESOLUTION; BOCN; BEARING; PSEUDOPEPTIDES; DERIVATIVES; IRON(II)-MEDIATED NITRENE TRANSFER; Sulfoximide; Stille coupling; Hydroxylamine; Catalytic reaction; Transition element complexes; Peptides; Sulfone; Palladium complex; Morpholine derivatives; Chemical substitution; Chemical coupling; Pseudopeptide; Suzuki coupling; Sulfinate; Asymmetric synthesis; Imination; Stereospecificity; Aromatic compound; Chemical synthesis; Oxygen nitrogen heterocycle
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo047940c

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.