title: Highly stereoselective and scalable synthesis of trans-fused octahydrocyclohepta[b]pyrrol-4(1H)-ones via the aza-Cope-Mannich rearrangement in racemic and enantiopure forms.
abstract: We have developed an efficient and stereoselective route to trans-fused octahydrocyclohepta[b]pyrrol-4(1H)-ones. The key features of our synthesis include the regioselective epoxide ring-opening of alkynyl oxiranes and a stereoselective aza-Cope-Mannich reaction. The target compounds were prepared in 3-6 steps from commercially available starting materials (61-75% overall yield) with minimal chromatographic purification. We have devised an stereoselective route to target compounds using Shi epoxidation or (R)-1-phenylethylamine as a source of chirality.
authors.affiliation: Department of Chemistry, Lomonosov Moscow State University, 1/3 Leninsky Gory, Moscow, 119991, Russia.
authors.forename: Dmitry S
authors.initials: DS
authors.lastname: Belov
authors.forename: Evgeny R
authors.initials: ER
authors.lastname: Lukyanenko
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Kurkin
authors.forename: Marina A
authors.initials: MA
authors.lastname: Yurovskaya
mesh_terms: D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003508:Cycloheptanes; D004852:Epoxy Compounds; D011758:Pyrroles