title: Enantioselective synthesis of 2,5-dihydrobenzo[b]azepine derivatives via iridium-catalyzed asymmetric allylic amination with 2-allylanilines and ring-closing-metathesis reaction.
abstract: Iridium-catalyzed asymmetric allylic amination of allylic carbonates with 2-allylanilines was realized. With a catalyst generated from 2 mol% of [Ir(dbcot)Cl](2) (dbcot = dibenzo[a,e]cyclooctatetraene) and 4 mol% of phosphoramidite ligand (L3), the amination products were obtained in up to 99% yield and 99% ee. Subjecting amination products to trifluoroacetyl protection and ring-closing-metathesis reaction provided an efficient synthesis of enantioenriched 2,5-dihydrobenzo[b]azepine derivatives.
authors.affiliation: State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling, Shanghai, 200032, PR China.
authors.forename: Ke-Yin
authors.initials: KY
authors.lastname: Ye
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Dai
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: You
mesh_terms: D000586:Amination; D000814:Aniline Compounds / Q000737:chemistry*; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D007495:Iridium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000814:Aniline Compounds; D001552:Benzazepines; D007495:Iridium; C023650:aniline