title: Dynamic thermodynamic resolution: solvent effects, mechanism, and an asymmetric 3,4,5-substituted benzazepine synthesis.
abstract: [reaction: see text] The resolution in the lithiation-substitution sequence from 1 to 4-11 in MTBE is shown to be under thermodynamic control in contrast to the previous report of kinetic control in diethyl ether. Diastereomeric equilibration of a soluble complex is shown to be controlling and an asymmetric synthesis of a 3,4,5-substituted benzazepine is reported.
authors.affiliation: Department of Chemistry, Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 61801, USA.
authors.forename: Yong Sun
authors.initials: YS
authors.lastname: Park
authors.forename: Eul Kgun
authors.initials: EK
authors.lastname: Yum
authors.forename: Amit
authors.initials: A
authors.lastname: Basu
authors.forename: Peter
authors.initials: P
authors.lastname: Beak
mesh_terms: D001552:Benzazepines / Q000138:chemical synthesis*; D002384:Catalysis; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D012997:Solvents; D013816:Thermodynamics
chemical_list: D001552:Benzazepines; D012997:Solvents; D008094:Lithium