On the enantioselective olefin epoxidation by doubly bridged biphenyl azepine derivatives--mixed tropos/atropos chiral biaryls.
Diastereomeric doubly bridged biphenyl azepines, atropos at 20 degrees C and tropos at 80 degrees C, are precursors to effective iminium organocatalysts that are employed in the enantioselective epoxidation of prochiral olefins (up to 85% ee).
Vachon
Jérôme
J
Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland.
Rentsch
Samuel
S
Martinez
Alexandre
A
Marsol
Claire
C
Lacour
Jérôme
J
D000475:Alkenes / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D007097:Imines / Q000737:chemistry; D007700:Kinetics; D008956:Models, Chemical; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics
D000475:Alkenes; D001381:Azepines; D001713:Biphenyl Compounds; D004852:Epoxy Compounds; D007097:Imines; C010574:biphenyl