Dynamic thermodynamic resolution: solvent effects, mechanism, and an asymmetric 3,4,5-substituted benzazepine synthesis.
[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.
Park
Yong Sun
YS
Department of Chemistry, Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 61801, USA.
Yum
Eul Kgun
EK
Basu
Amit
A
Beak
Peter
P
D001552:Benzazepines / Q000138:chemical synthesis*; D002384:Catalysis; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D012997:Solvents; D013816:Thermodynamics
D001552:Benzazepines; D012997:Solvents; D008094:Lithium