title: Synthesis of 1,5-benzothiazepine dipeptide mimetics via two CuI-catalyzed cross coupling reactions.
abstract: CuI-catalyzed coupling of 4-methylphenyl bromide with amino acids gives N-aryl amino acids, which are converted into linear dipeptides via iodination and condensation with L-cysteine derived acyl chloride. Cyclization is achieved via a CuI/N,N-dimethylglycine catalyzed intramolecular coupling of aryl iodides with the liberated thiol to afford 1,5-benzothiazepine dipeptide mimetics.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
authors.forename: Jiangang
authors.initials: J
authors.lastname: Gan
authors.forename: Dawei
authors.initials: D
authors.lastname: Ma
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C106746:1,5-benzothiazepine; D004151:Dipeptides; D007454:Iodides; D013841:Thiazepines; D003300:Copper; C073870:cuprous iodide